A rearrangement approach to (+/-)-cerapicol

Authors
El-Hachach, N Fischbach, M Gerke, R Fitjer, L
Citation
N. El-hachach et al., A rearrangement approach to (+/-)-cerapicol, TETRAHEDRON, 55(19), 1999, pp. 6119-6128
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
19
Year of publication
1999
Pages
6119 - 6128
Database
ISI
SICI code
0040-4020(19990507)55:19<6119:ARAT(>2.0.ZU;2-P
Abstract
The synthesis and rearrangement of the cyclobutyl methanol 4 is described. The synthesis has been achieved by addition of the Grignard reagent 16 to t he bicyclic ketone 22. Experimental procedures for the preparation of both compounds are given. Upon treatment with trifluoroacetic acid and subsequen t reduction, 4 yields the norbornanes 24 and 25 and (+/-)-cerapicol (8). So me consequences concerning the search for other potential precursors of 8 a re discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.