Oxetanes as versatile building blocks in the total synthesis of natural products: An overview

Ahmed Mahal

doi:10.5155/eurjchem.6.3.357-366.1267

PDF

Published: Sep 30, 2015

DOI: https://doi.org/10.5155/eurjchem.6.3.357-366.1267

Keywords:

Oxetane, Anti-tumor, Drug discovery, Small molecules, Natural products, Heterocyclic synthesis

Section

Review Article

Issue

Vol. 6 No. 3 (2015): September 2015

Dates

Received 2015-04-27
Accepted 2015-06-01
Published 2015-09-30

Ahmed Mahal

Department of Chemistry of the Natural Products, School of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Napoli, Italy

Abstract

Oxetane ring plays an important role as main core in naturally occurring compounds and has many applications in pharmaceutical industries and synthetic organic chemistry. In this review, we report a brief survey of using the oxetane ring as versatile precursors in the total synthesis of natural products. Many approaches such as cyclization, addition, oxidation, reduction, elimination, protection as well as deprotection reactions utilized to synthesize of most important oxetane-containing natural products involving taxol, (±)-merrilactone A, (±)-oxetin, L-oxetanocin, (+)-(Z)-laureatin and L-oxetanocin are also covered. We describe in this review the most common total synthesis approaches have been yet applied to synthesis of most important oxetane-containing natural products. The review is also included isolation, structure Identification of these oxetane-containing natural products. The biological activity of oxetane-containing natural products due to the oxetane ring is also defined.

This Abstract was viewed 9317 times |

Article PDF downloaded 1282 times

How to Cite

(1)

Mahal, A. Oxetanes As Versatile Building Blocks in the Total Synthesis of Natural Products: An Overview. Eur. J. Chem. 2015, 6, 357-366.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Wang, M.; Cornett, B.; Nettles, J.; Liotta, D. C.; Snyder, J. P. J. Org. Chem. 2000, 65, 1059-1068.
http://dx.doi.org/10.1021/jo9916075

[2]. Burkhard, J. A.; Wuitschik, G.; Rogers-Evans, M.; Müller, K.; Carreira, E. M. Angew. Chem. Int. Ed. 2010, 49, 9052-9067.
http://dx.doi.org/10.1002/anie.200907155

[3]. Davis, O. A.; Bull, J. A. Angew. Chem. Int. Ed. 2014, 53, 14230-14234.
http://dx.doi.org/10.1002/anie.201408928

[4]. Li, C.; Lee, D.; Graf, T. N.; Phifer, S. S.; Nakanishi, Y.; Burgess, J. P.; Riswan, S.; Setyowati, F. M.; Saribi, A. M.; Soejarto, D. D.; Farnsworth, N. R.; Falkinham III, J. O.; Kroll, D. J.; Kinghorn, A. D.; Wani, M. C.; Oberlies, N. H. Org. Lett. 2005, 7, 5709-5712.
http://dx.doi.org/10.1021/ol052498l

[5]. Han, Q. B.; Zhang, J. X.; Lu, Y.; Wu, Y. S.; Zheng, Q. T.; Sun, H. D. Planta Med. 2004, 70, 581-584.
http://dx.doi.org/10.1055/s-2004-827165

[6]. Pullaiah, K. C.; Surapaneni, R. K.; Rao, C. B.; Albizati, K. F.; Sullivan, B. W.; Faulkner, D. J.; He, C. H.; Clardy, J. J. Org. Chem. 1985, 50, 3665-3666.
http://dx.doi.org/10.1021/jo00219a057

[7]. Reinecke, J.; Hoffmann, H. M. R. Chem. Eur. J. 1995, 1, 368-373.
http://dx.doi.org/10.1002/chem.19950010607

[8]. Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135-9145.
http://dx.doi.org/10.1021/jo961680k

[9]. Wittenberg, J.; Beil, W.; Hoffmann, H. M. R. Tetrahedron Lett. 1998, 39, 8259-8262.
http://dx.doi.org/10.1016/S0040-4039(98)01886-3

[10]. Proemmel, S.; Wartchow, R.; Hoffmann, H. M. R. Tetrahedron 2002, 58, 6199-6206.
http://dx.doi.org/10.1016/S0040-4020(02)00622-1

[11]. Loh, L.; Carlson, R. W.; York, W. S.; Stacey, G. Proc. Natl. Acad. Sci. 2002, 99, 14446-14451.
http://dx.doi.org/10.1073/pnas.222336799

[12]. Shimada, N.; Hasegawa, S.; Harada, T.; Tomisawa, T.; Fujii, A.; Takita, T. J. Antibiot. 1986, 39, 1623-1625.
http://dx.doi.org/10.7164/antibiotics.39.1623

[13]. Hoshino, H.; Shimizu, N.; Shimada, N.; Takita, T.; Takeuchi, T. J. Antibiot. 1987, 40, 1077-1078.
http://dx.doi.org/10.7164/antibiotics.40.1077

[14]. Niitsuma, S.; Ichikawa, Y.; Kato, K.; Takita, T. Tetrahedron Lett. 1987, 28, 3967-3970.
http://dx.doi.org/10.1016/S0040-4039(00)96433-5

[15]. Niitsuma, S.; Ichikawa, Y.; Kato, K.; Takita, T. Tetrahedron Lett. 1987, 28, 4713-4714.
http://dx.doi.org/10.1016/S0040-4039(00)96606-1

[16]. Ichikawa, E.; Kato, K. Synthesis 2002, 2002, 1-28.

[17]. Wilson, F. X.; Fleet, G. W. J.; Vogt, K.; Wang, Y.; Witty, D. R.; Choi, S.; Storer, R.; Myers, P. L.; Wallis, C. J. Tetrahedron Lett. 1990, 31, 6931-6934.
http://dx.doi.org/10.1016/S0040-4039(00)97210-1

[18]. Saksena, A. K.; Ganguly, A. K.; Girijavallabhan, V. M.; Pike, R. E.; Chen, Y.; Puar, M. S. Tetrahedron Lett. 1992, 33, 7721-7724.
http://dx.doi.org/10.1016/0040-4039(93)88027-G

[19]. Norbeck, D. W.; Kramer, J. B. J. Am. Chem. Soc. 1988, 110, 7217-7218.
http://dx.doi.org/10.1021/ja00229a048

[20]. Gumina, G.; Chu, C. K. Org. Lett. 2002, 4, 1147-1149.
http://dx.doi.org/10.1021/ol025562x

[21]. Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 17, 3535-3536.
http://dx.doi.org/10.1016/S0040-4039(00)71351-7

[22]. Pudlo, J. S.; Townsend, L. B. Nucleic Acid Chemistry, Part 4; Townsend, L. B.; Tipson, R. S. Eds.; Wiley: New York, 1978; pp. 1151.

[23]. Saksena, A. K.; Ganguly, A. k.; Girijavallabhan, V. M.; Pike, R. E.; Chen, Y. T.; Puar, M. S. Tetrahedron Lett. 1992, 33, 7721-7724.
http://dx.doi.org/10.1016/0040-4039(93)88027-G

[24]. Omura, S.; Murata, M.; Imamura, N.; Iwai, Y.; Tanaka, H.; Furusaki, A.; Matsumoto, T. J. Antibiot. 1984, 37, 1324-1332.
http://dx.doi.org/10.7164/antibiotics.37.1324

[25]. Kawahata, Y.; Takatsuto, S.; Ikekawa, N.; Murata, M.; Omura, S. Chem. Pharm. Bull. 1986, 34, 3102-3110.
http://dx.doi.org/10.1248/cpb.34.3102

[26]. Tomoda, H.; Omura, S. J. Antibiot. 1990, 43, 1207-1022.
http://dx.doi.org/10.7164/antibiotics.43.1207

[27]. Bach, T.; Schröder, J. Eur. J. Org. Chem. 1997, 11, 2265-2267.

[28]. Kelly, T. R.; Schmidt, T. E.; Haggerty, J. G. Synthesis 1972, 544-545.
http://dx.doi.org/10.1055/s-1972-21915

[29]. Meth-Cohn, K. T.; Westwood, T. J. Chem. Soc. Perkin Trans. 1 1984, 1173-1182.
http://dx.doi.org/10.1039/p19840001173

[30]. Huang, J. M.; Yokoyama, R.; Yang, C. S.; Fukuyama, Y. Tetrahedron Lett. 2000, 41, 6111-6114.
http://dx.doi.org/10.1016/S0040-4039(00)01023-6

[31]. Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080-2081.
http://dx.doi.org/10.1021/ja012495d

[32]. Inoue, M; Sato, T; Hirama, M. J. Am. Chem. Soc. 2003, 125, 10772-10773.
http://dx.doi.org/10.1021/ja036587+

[33]. Meng, Z.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2005, 44, 1511-1513.
http://dx.doi.org/10.1002/anie.200462509

[34]. Inoue, M.; Sato, T.; Hirama, M. Angew. , Chem. Int. Ed. 2006, 45, 4843-4548.
http://dx.doi.org/10.1002/anie.200601358

[35]. He, W.; Huang, J.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 300-308.
http://dx.doi.org/10.1021/ja0761986

[36]. Mehta, G.; Singh, S. R. Angew. Chem. 2006, 118, 967-969.
http://dx.doi.org/10.1002/ange.200503618

[37]. Inoue, M.; Lee, N.; Kasuya, S.; Sato, T.; Hirama, M.; Moriyama, M.; Fukuyama, Y. J. Org. Chem. 2007, 72, 3065-3075.
http://dx.doi.org/10.1021/jo0700474

[38]. Harada, K.; Kato, H.; Fukuyama, Y. Tetrahedron Lett. 2005, 46, 7407-7410.
http://dx.doi.org/10.1016/j.tetlet.2005.08.116

[39]. Harada, K.; Ito, H.; Hioki, H.; Fukuyama, Y. Tetrahedron Lett. 2007, 48, 6105-6108.
http://dx.doi.org/10.1016/j.tetlet.2007.06.159

[40]. Iriondo-Alberdi, J.; Perea-Buceta, J. E.; Greaney, M. F. Org. Lett. 2005, 7, 3969-3971.
http://dx.doi.org/10.1021/ol0514496

[41]. Schenck, G. O.; Hartmann, W.; Steinmetz, R. Chem. Ber. 1963, 96, 498-508.
http://dx.doi.org/10.1002/cber.19630960222

[42]. Gauvry, N.; Comoy, C.; Lescop, C.; Huet, F. Synthesis 1999, 574-576
http://dx.doi.org/10.1055/s-1999-3441

[43]. Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198-2200.
http://dx.doi.org/10.1021/jo00212a041

[44]. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857
http://dx.doi.org/10.1021/ja00074a085

[45]. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
http://dx.doi.org/10.1021/ja952676d

[46]. Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
http://dx.doi.org/10.1002/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G

[47]. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
http://dx.doi.org/10.1021/ar000114f

[48]. Balskus, E. P.; Mendez-Andino, J.; Arbit, R. M.; Paquette, L. A. J. Org. Chem. 2001, 66, 6695-6704.
http://dx.doi.org/10.1021/jo010494y

[49]. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022.
http://dx.doi.org/10.1016/0040-4039(94)80038-3

[50]. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
http://dx.doi.org/10.1021/jo00127a036

[51]. Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547-2549.
http://dx.doi.org/10.1021/ja00242a068

[52]. Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415-3434.
http://dx.doi.org/10.1021/cr010001p

[53]. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566.
http://dx.doi.org/10.1021/ja00384a082

[54]. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742.
http://dx.doi.org/10.1021/ja00349a082

[55]. Zhang, W. Tetrahedron 2001, 57, 7237-7262.
http://dx.doi.org/10.1016/S0040-4020(01)00634-2

[56]. Danishefsky, S.; Kitahara, T.; McKee, R.; Schuda, P. F. J. Am. Chem. Soc. 1976, 98, 6715-6717.
http://dx.doi.org/10.1021/ja00437a058

[57]. Crisp, G. T.; Scott, W. J. Synthesis 1985, 1985, 335-337.

[58]. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
http://dx.doi.org/10.1016/S0040-4039(00)60957-7

[59]. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821-4824.
http://dx.doi.org/10.1016/S0040-4039(01)81529-X

[60]. Fetizon, M.; Golfier, M. Compt. Rend. 1968, 267, 900-903.

[61]. McKillop, A.; Young, D. W. Synthesis 1979, 401-422.
http://dx.doi.org/10.1055/s-1979-28699

[62]. Murray, R. W. Chem. Rev. 1989, 89, 1187-1201.
http://dx.doi.org/10.1021/cr00095a013

[63]. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
http://dx.doi.org/10.1021/ar00162a002

[64]. Irie, T.; Izawa, M.; Kurosawa, E. Tetrahedron, 1970, 26, 851-870.
http://dx.doi.org/10.1016/S0040-4020(01)97884-6

[65]. Irie, T.; Izawa, M.; Kurosawa, E. Tetrahedron Lett. 1968, 9, 2091-2096.
http://dx.doi.org/10.1016/S0040-4039(00)89750-6

[66]. Sugimoto, M.; Suzuki, T.; Hagiwara, H.; Hoshi, T. Tetrahedron Lett. 2007, 48, 1109-1112.
http://dx.doi.org/10.1016/j.tetlet.2006.12.082

[67]. Keshipeddy, S.; Martinez, I.; Castillo II, F. B.; Morton, M. D.; Howell, R. A. J. Org. Chem. 2012, 77, 7883-7890.
http://dx.doi.org/10.1021/jo301048z

[68]. Kim, H.; Lee, H.; Lee, D.; Kim, S.; Kim, D. J. Am. Chem. Soc. 2007, 129, 2269-2274.
http://dx.doi.org/10.1021/ja068346i

[69]. Ishihara, J.; Shimada, Y.; Kanoh, N.; Takasugi, Y.; Fukuzawa, A.; Murai, A. Tetrahedron 1997, 53, 8371-8382.
http://dx.doi.org/10.1016/S0040-4020(97)00542-5

[70]. Ishihara, J.; Kanoh, N.; Murai, A. Tetrahedron Lett. 1995, 36, 737-740.
http://dx.doi.org/10.1016/0040-4039(94)02329-A

[71]. Fukuzawa, A.; Aye, M.; Takasugi, Y.; Nakamura, M.; Tamura, M.; Murai, A. Chem. Lett. 1994, 2307-2310.
http://dx.doi.org/10.1246/cl.1994.2307

[72]. Murai, A.; Ono, M.; Masamune, T. Bull. Chem. Soc. Jpn. 1977, 50, 1226-1231.
http://dx.doi.org/10.1246/bcsj.50.1226

[73]. Torisawa, Y.; Okabe, H.; Ikegami, S. Chem. Lett. 1984, 13, 1555-1556.
http://dx.doi.org/10.1246/cl.1984.1555

[74]. Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348.
http://dx.doi.org/10.1016/S0040-4039(00)74256-0

[75]. Fujiwara, K.; Akakura, D.; Tsunashima, M.; Nakamura, A.; Honma, T.; Murai, A. J. Org. Chem. 1999, 64, 2616-2617.
http://dx.doi.org/10.1021/jo990212i

[76]. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772.
http://dx.doi.org/10.1016/S0040-4039(01)94157-7

[77]. Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1996, 61, 5716-5717.
http://dx.doi.org/10.1021/jo961013r

[78]. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4465-4470.
http://dx.doi.org/10.1016/S0040-4039(00)91094-3

[79]. Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44.
http://dx.doi.org/10.1002/anie.199400151

[80]. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggen, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
http://dx.doi.org/10.1021/ja00738a045

[81]. Lavelle, F. Curr. Opin. Invest. Drugs 1993, 2, 627-635.

[82]. Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Semin. Oncol. 1992, 19, 646-662.

[83]. Holmes, F. A.; Waters, R. J.; Theriault, R. I.; Forman, A. D.; Newton, L. K.; Raber, M. N.; Buzdar, A. U.; Frye, D. K.; Hortobagyi, G. N. J. Natl. Cancer Inst. U. S. A. 1991, 83, 1797-1805.
http://dx.doi.org/10.1093/jnci/83.24.1797-a

[84]. McGuire, W. P.; Rowinsky, E. K.; Rosenshein, N. B.; Grumbine, F. C.; Ettinger, D. S.; Armstrong, D. K.; Donehower, R. C. Ann. Intern. Med. 1989, 111, 273-279.
http://dx.doi.org/10.7326/0003-4819-111-4-273

[85]. Einzig, A. I.; Wiemik, P. H.; Sasloff, J.; Garl, S.; Runowicz, C.; O'Hanlan, K. A.; Goldberg, G. Proc. Am. Assoc. Cancer Res. 1990, 31, 187-187.

[86]. Pazdur, R.; Ho, D. H.; Lassere, Y.; Bready, B.; Kvakoff, I. H.; Raber, M. N. Proc. Am. Soc. Clin. Oncol. 1992, 11, 111-111.

[87]. Caldas, C.; McGuire, W. P. III. Semin. Oncol. 1993, 20 (4-3), 50-55.

[88]. Einzig, A. I.; Hochster, H.; Wiemik, P. H.; Trump, D. L.; Dutcher, J. P.; Garowski, E.; Sasloff, J.; Smith. T. J. Invest. New Drugs 1991, 9, 59-64.

[89]. Legha, S. S.; Ring, S.; Papadopoulos, N.; Raber, M. N.; Benjamin, R. Cancer 1990, 65, 2478-2481.
http://dx.doi.org/10.1002/1097-0142(19900601)65:11<2478::AID-CNCR2820651114>3.0.CO;2-S

[90]. Chang, A.; Kim, K.; Glick, J.; Anderson, T.; Karp, D.; Johnson, D. J. Natl. Cancer Inst. 1993, 85, 388-394.
http://dx.doi.org/10.1093/jnci/85.5.388

[91]. Murphey, W. K.; Winn, R. J.; Fossella, F. V.; Shin, D. M.; Hynes, H. E.; Gross, H. M.; Davila, E.; Leimert, J. T.; Dhinga, H. M.; Raber, M. N.; Krakoff, I. H.; Hong, W. K. Proc. Am. Soc. Clin. Oncol. 1993, 85, 384-388.

[92]. Ettinger, D. S. Semin. Oncol. 1993, 20 (4-3), 46-49.

[93]. Forastiere, A. A. Semin. Oncol. 1993, 20 (4-3), 56-60.

[94]. Nicolaou, K. C.; Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan, E. J. Sorenson. Nature, 1994, 367, 630-634.
http://dx.doi.org/10.1038/367630a0

[95]. Holton, R. H.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, Y.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598.
http://dx.doi.org/10.1021/ja00083a066

[96]. Holton, R. H.; Kim, H. B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600.
http://dx.doi.org/10.1021/ja00083a067

[97]. Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. G. J. Am. Chem. Soc. 1996, 118, 2843-2859.
http://dx.doi.org/10.1021/ja952692a

[98]. Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Gränicher, C.; Houze, J. B.; Jänichen, J.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Mucciaro, T. P.; Mühlebach, M.; Natchus, M. G.; Paulsen, H.; Rawlins, D. B.; Satkofsky, J.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E.; Tomooka, K. J. Am. Chem. Soc. 1997, 119, 2755-2756.
http://dx.doi.org/10.1021/ja9635387

[99]. Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758.
http://dx.doi.org/10.1021/ja963539z

[100]. Morihira, K.; Hara, R.; Kawahara, S.; Nishimori, T.; Nakamura, N.; Kusama, H.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 12980-12981.
http://dx.doi.org/10.1021/ja9824932

[101]. Morihira, K.; Hara, R.; Kawahara, S.; Nishimori, T.; Kashima, H.; Nakamura, N.; Morihira, K.; Kuwajima, I. J. Am. Chem. Soc. 2000, 122, 3811-3820.
http://dx.doi.org/10.1021/ja9939439

[102]. Shiina, I.; Iwadare, H.; Sakoh, H.; Hasegawa, M.; Tani, Y. I.; Mukaiyama, T. Chem. Lett. 1998. 27, 1-2.
http://dx.doi.org/10.1246/cl.1998.1

[103]. Doi, T.; Fuse, S.; Miyamoto, S.; Nakai, K.; Sasuga, D.; Takahashi, T.; Chem. Asian J. 2006, 1, 370-383.
http://dx.doi.org/10.1002/asia.200600156

[104]. Nicolaou, K. C.; Nantermet, P. G.; Ueno H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633.
http://dx.doi.org/10.1021/ja00107a006

[105]. Nicolaou, K. C.; Liu, J. J.; Yang, Z.; Ueno, H.; Sorensen, E. J.; Claiborne, C. F.; Guy, R. K.; Hwang, C. K.; Nakada M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634-644.
http://dx.doi.org/10.1021/ja00107a007

[106]. Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Nantermet, P. G.; Claiborne, C. F.; Renaud, J.; Guy, R. K.; Shibayama, K. J. Am. Chem. Soc. 1995, 117, 645-652.
http://dx.doi.org/10.1021/ja00107a008

[107]. Nicolaou, K. C.; Ueno, H.; Liu, J. J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659.
http://dx.doi.org/10.1021/ja00107a009

[108]. Ettouati, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823-9838.
http://dx.doi.org/10.1016/S0040-4020(01)80721-3

[109]. Magee, T. V.; Bornmann, W. G.; Isaccs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274-3276.
http://dx.doi.org/10.1021/jo00038a008

Supporting Agencies

University of Naples Federico II, Napoli, Italy

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Downloads

Metrics