

A simple stereoselective synthesis of (+)-[6]-gingerdiol
Rathod Aravind Kumar (1)




(1) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(2) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(3) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(4) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(*) Corresponding Author
Received: 11 Mar 2013 | Revised: 03 Apr 2013 | Accepted: 12 Apr 2013 | Published: 30 Sep 2013 | Issue Date: September 2013
Abstract
A simple stereoselective synthesis of (+)-[6]-gingerdiol has been accomplished starting from vanillin. The synthetic sequence involves Mouroka allylation, diasterioselective iodine induced electrophilic cyclization and ring-opening of an epoxide as the key steps.

Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.4.3.191-194.768
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Funding information
Council of Scientific and Industrial Research and University Grants Commission, New Delhi, India
Citations
[1]. Sachin B. Markad, Viraj A. Bhosale, Suvarna R. Bokale, Suresh B. Waghmode
Stereoselective Approach towards the Synthesis of 3R, 5 S Gingerdiol and 3 S, 5 S Gingerdiol
ChemistrySelect 4(2), 502, 2019
DOI: 10.1002/slct.201803154

[2]. Sunita Gamre, Mrityunjay Tyagi, Sucheta Chatterjee, Birija S. Patro, Subrata Chattopadhyay, Dibakar Goswami
Synthesis of Bioactive Diarylheptanoids from Alpinia officinarum and Their Mechanism of Action for Anticancer Properties in Breast Cancer Cells
Journal of Natural Products 84(2), 352, 2021
DOI: 10.1021/acs.jnatprod.0c01012

References
[1]. Murata, T.; Shinohara, M.; Miyamoto, M. Chem. Pharm. Bull. 1972, 20, 2291-2292.
http://dx.doi.org/10.1248/cpb.20.2291
[2]. Kikuzaki, H.; Tsai, S.-M.; Nakatani, N. Phytochemistry. 1992, 31, 1783-1786.
http://dx.doi.org/10.1016/0031-9422(92)83147-Q
[3]. Sekiva, Y.; Kubota, K.; Kobayashi, A. J. Agric. Food Chem. 2000, 48, 373-377.
http://dx.doi.org/10.1021/jf990674x
[4]. Schuhbaum, H.; Burgermeister, J.; Paper, D. H.; Franz, G. Pharmaceu. Pharmocol. Lett. 2000, 10, 82-85.
[5]. Ficker, C.; Smith, M. L.; Apkagana, K.; Glessor, M.; Zhang, H.; Durst, H.; Assabgui, R.; Arnason, J. T. Phytother Res. 2003, 17, 897-902.
http://dx.doi.org/10.1002/ptr.1335
PMid:13680820
[6]. Franck-Neumann, M.; Geoffroy, P.; Bissinger, P.; Adelaide, S. Tetrahedron Lett. 2001, 42, 6401-6404.
http://dx.doi.org/10.1016/S0040-4039(01)01263-1
[7]. Das, B.; Krishnaiah, M.; Nagendra, S.; Reddy, Ch, R. Lett. Org. Chem. 2011, 8, 244-248.
http://dx.doi.org/10.2174/157017811795371494
[8]. Das, B.; Balasubramanyam, P.; Veeranjaneyulu, B.; Reddy, G. C. Helv. Chem. Acta. 2011, 94, 881-884.
http://dx.doi.org/10.1002/hlca.201000342
[9]. Das, B.; Kumar, D. N. Synlett. 2011, 1285-1287.
http://dx.doi.org/10.1055/s-0030-1260546
[10]. Satyalakshmi, G.; Suneel, K.; Shinde, B. D.; Das, B. Tetrahedron: Asymm. 2011, 22, 1000-1005.
http://dx.doi.org/10.1016/j.tetasy.2011.06.011
[11]. Das, B.; Laxminarayana, K.; Krishnaiah, M.; Kumar, D. N. Helv. Chem. Acta. 2009, 92, 1840-1844.
http://dx.doi.org/10.1002/hlca.200900083
[12]. Nagendra, S.; Krishnaiah, M.; Reddy, K. R.; Das, B. Eur. J. Chem. 2012, 3, 337-339.
http://dx.doi.org/10.5155/eurjchem.3.3.337-339.609
[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.; Predows, J. D.; Brown, E. G.; Morimoto, A.; Jernstedt, K, K. J. Org. Chem. 1982, 47, 4013-4018.
[15]. Bougini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626-4633.
http://dx.doi.org/10.1021/jo00145a004
[16]. Kumar, P.; Gupta, P.; Naidu, S. V. Chem. Eur. J. 2006, 12, 1397-1402.
http://dx.doi.org/10.1002/chem.200501029
PMid:16308881
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.4.3.191-194.768

















European Journal of Chemistry 2013, 4(3), 191-194 | doi: https://doi.org/10.5155/eurjchem.4.3.191-194.768 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.