ENANTIOSELECTIVE SYNTHESIS OF CADINANES STARTING FROM R-(-)-OR S-(-CARVONE())

Authors
BARANOVSKY AV JANSEN BJM MEULEMANS TM DEGROOT A
Citation
Av. Baranovsky et al., ENANTIOSELECTIVE SYNTHESIS OF CADINANES STARTING FROM R-(-)-OR S-(-CARVONE()), Tetrahedron, 54(21), 1998, pp. 5623-5634
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
21
Year of publication
1998
Pages
5623 - 5634
Database
ISI
SICI code
0040-4020(1998)54:21<5623:ESOCSF>2.0.ZU;2-S
Abstract
A new enantioselective synthesis of cadinanes, using the Mukaiyama-Mic hael reaction, was developed starting from R-(-)- or S-(+)-carvone. Th is approach gives an easy and direct access to the cadinane skeleton a nd the scope proved to be complementary to a formylation-annelation se quence. The applicability of the method was demonstrated by the enanti oselective synthesis of 1,9-cadinadien-3-one and 4-methoxy-1,9-cadinad ien-3-one. (C) 1998 Elsevier Science Ltd. All rights reserved.