Diastereoselective synthesis of an advanced intermediate of thapsigargin and other 6,12-guaianolides using a RCEYM strategy

Jouanneau, M., Bonepally, K. R., Jeuken, A., Tap, A., Guillot, R., Ardisson, J., Férézou, J.-P. and Prunet, J. (2018) Diastereoselective synthesis of an advanced intermediate of thapsigargin and other 6,12-guaianolides using a RCEYM strategy. Organic Letters, 20(8), pp. 2176-2180. (doi: 10.1021/acs.orglett.8b00456) (PMID:29616815)

Abstract

A new and flexible approach toward the synthesis of 6,12-guaianolide anticancer drugs such as trilobolides or thapsigargin has been developed that could be applied to the preparation of analogues with a modified ring system. The synthesis starts from commercial 2-methylcyclopentane-1,3-dione, only relying on diastereoselective reactions for the construction of the stereogenic centers at C1, C3, C6, and C10 and features a high-yielding ring-closing enyne metathesis (RCEYM) step for the formation of the [5,7] bicyclic core.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Jeuken, Alan and Prunet, Dr Joelle
• Authors: Jouanneau, M., Bonepally, K. R., Jeuken, A., Tap, A., Guillot, R., Ardisson, J., Férézou, J.-P., and Prunet, J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 04 April 2018
• Copyright Holders: Copyright © 2018 American Chemical Society
• First Published: First published in Organic Letters 20(8): 2176-2180
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher