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Concise total synthesis of (±)-palominol and (±)-dolabellatrienone via a dianion-accelerated oxy-cope rearrangement

Authors :
E. J. Corey
Robert S. Kania
Source :
Tetrahedron Letters. 39:741-744
Publication Year :
1998
Publisher :
Elsevier BV, 1998.

Abstract

A short synthesis of (±)-palominol (1) and (±)-dolabellatrienone (2) starting from farnesol is reported. Noteworthy steps include an intramolecular pinacol coupling to form a 15-membered carbocyclic diol and subsequent dianion-accelerated oxy-Cope rearrangement to form the 11,5-trans-fused ring system of the dolabellanes.

Details

ISSN :
00404039
Volume :
39
Database :
OpenAIRE
Journal :
Tetrahedron Letters
Accession number :
edsair.doi...........c0ecebef69187b53eb3f8d4f95b9e5b4
Full Text :
https://doi.org/10.1016/s0040-4039(97)10614-1