CONCISE TOTAL SYNTHESIS OF (-PALOMINOL AND (+())-)-DOLABELLATRIENONE VIA A DIANION-ACCELERATED OXY-COPE REARRANGEMENT/

Authors
COREY EJ KANIA RS
Citation
Ej. Corey et Rs. Kania, CONCISE TOTAL SYNTHESIS OF (-PALOMINOL AND (+())-)-DOLABELLATRIENONE VIA A DIANION-ACCELERATED OXY-COPE REARRANGEMENT/, Tetrahedron letters, 39(8), 1998, pp. 741-744
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
8
Year of publication
1998
Pages
741 - 744
Database
ISI
SICI code
0040-4039(1998)39:8<741:CTSO(A>2.0.ZU;2-T
Abstract
A short synthesis of (+/-)-palominol (1) and (+/-)-dolabellatrienone ( 2) starting from farnesol is reported. Noteworthy steps include an int ramolecular pinacol coupling to form a 15-membered carbocyclic diol an d subsequent dianion-accelerated oxy-Cope rearrangement to form the 11 ,5-trans-fused ring system of the dolabellanes. (C) 1998 Elsevier Scie nce Ltd. All rights reserved.