High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (+/-)-beta-necrodol

Authors
Samajdar, S Ghatak, A Banerjee, S Ghosh, S
Citation
S. Samajdar et al., High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (+/-)-beta-necrodol, TETRAHEDRON, 57(10), 2001, pp. 2011-2014
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
10
Year of publication
2001
Pages
2011 - 2014
Database
ISI
SICI code
0040-4020(20010303)57:10<2011:HDICRI>2.0.ZU;2-G
Abstract
Total synthesis of the monoterpene beta -necrodol has been accomplished. Th e key step involves an ortho-ester Claisen rearrangement in a highly steric ally congested cyclopentane derivative resulting in a high level of 1,3-tra ns diastereoselection. A novel photo-induced decarboxylation of the obtaine d gamma,delta -unsaturated acid afforded beta -necrodol. (C) 2001 Elsevier Science Ltd. All rights reserved.