European Journal of Chemistry

A simple formal stereoselective synthesis of Herbarumin III



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Nagendra Siddavatam
Krishnaiah Martha
Krishna Reddy Vanka
Biswanath Das

Abstract

A formal stereoselective synthesis of Herbarumin III has been accomplished starting from butanal involving Maruoka asymmetric allylation, diastereoselective iodine-induced electrophilic cyclization and conversion of iodocarbonate into syn-epoxy alcohol as the key steps.

3_3_337_339_800


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Siddavatam, N.; Martha, K.; Vanka, K. R.; Das, B. A Simple Formal Stereoselective Synthesis of Herbarumin III. Eur. J. Chem. 2012, 3, 337-339.

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References

[1]. Rivero-Cruz, J. F.; Cerda-Garcia-Rojas, C. M.; Mata, R. J. Nat. Prod. 2003, 66, 511-514.
http://dx.doi.org/10.1021/np020501t
PMid:12713403

[2]. Gurjar, M. K.; Karmakar, S.; Mahapatra, D. K. Tetrahedron Lett. 2004, 45, 4525-4526.
http://dx.doi.org/10.1016/j.tetlet.2004.04.040

[3]. Gurjar, M. K.; Nagaprasad, R.; Ramana, C. V.; Mahapatra, D. K. Arkivoc 2005, 3, 237-257.

[4]. Nanda, S. Tetrahedron Lett. 2005, 46, 3661-3663.
http://dx.doi.org/10.1016/j.tetlet.2005.03.139

[5]. Boruwa, J.; Bogoi, N.; Barua, N. C. Org. Biomol. Chem. 2006, 4, 3521-3525.
http://dx.doi.org/10.1039/b605982a

[6]. Gupta, P.; Kumar, P. Tetrahedron: Asymmetr. 2007, 18, 1688-1692.
http://dx.doi.org/10.1016/j.tetasy.2007.07.022

[7]. Chen, X. S.; Da, S. J.; Yang, L. H.; Xu, B. Y.; Xie, Z. X.; Li, Y. Chin. Chem. Lett. 2007, 18, 255-257.
http://dx.doi.org/10.1016/j.cclet.2007.01.035

[8]. Yadav, J. S.; Atter, H.; Gayathri, K. U.; Rao, N. V.; Prasad, A. R. Synthesis 2008, 3945-3950.
http://dx.doi.org/10.1055/s-0028-1083249

[9]. Sabitha, G.; Srinivas, C.; Maruthi, C.; Yadav, J. S. Helv. Chim. Acta. 2010, 93, 1634-1640.
http://dx.doi.org/10.1002/hlca.200900427

[10]. Das, B.; Suneel, K.; Satyalaxmi, G.; Kumar, D. N. Tetrahedron: Asymmetr. 2009, 20, 1536-1540.
http://dx.doi.org/10.1016/j.tetasy.2009.05.036

[11]. Das, B.; Krishnaiah, M.; Sudhakar, C. Bioorg. Med. Chem. Lett. 2010, 20, 2303-2305.
http://dx.doi.org/10.1016/j.bmcl.2010.01.162

[12]. Das, B.; Kumar, D. N. Synlett 2011, 1285-1287.
http://dx.doi.org/10.1055/s-0030-1260546

[13]. Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
http://dx.doi.org/10.1021/ja020338o
PMid:12580590

[14]. Bartlett, P. A.; Meadows, J. D.; Brown. E. G.; Morimoto, A.; Jernstedt, K. K. J. Org. Chem. 1982, 47, 4013-4018.
http://dx.doi.org/10.1021/jo00142a002

[15]. Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626-4633.
http://dx.doi.org/10.1021/jo00145a004

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Council of Scientific and Industrial Research and University Grants Commission, New Delhi, India
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