An enantiospecific approach to thapsanes from R-carvone: synthesis of (-)-thaps-8-en-5-ol

Authors
Srikrishna, A Anebouselvy, K Reddy, TJ
Citation
A. Srikrishna et al., An enantiospecific approach to thapsanes from R-carvone: synthesis of (-)-thaps-8-en-5-ol, TETRAHEDR L, 41(34), 2000, pp. 6643-6647
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
34
Year of publication
2000
Pages
6643 - 6647
Database
ISI
SICI code
0040-4039(20000819)41:34<6643:AEATTF>2.0.ZU;2-I
Abstract
The first enantiospecific synthesis of a thapsane, containing three contigu ous quaternary carbon atoms, is accomplished starting from R-carvone. An in tramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of thre e contiguous quaternary carbon atoms present in the thapsane framework. (C) 2000 Published by Elsevier Science Ltd.