In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 90, No. 1 ( 2012-01), p. 75-84
Abstract:
1,3-Dimethyl-2-nitrobenzene was converted to the key intramolecular Friedel–Crafts intermediate 24 in ten steps. Treatment of 24 with TiCl 4 produced tricyclic enone 25 in 61%–75% yield, having the requisite trans relationship of the two angular methyl groups and many of the salient features of the dolastane diterpenes. The structure of enone 25 was verified by X-ray crystallography analysis. Cyclization product 25 permitted the facile synthesis of (±)-14-epi-hydroxydolasta-1(15),7,9-triene and (±)-7-epi-acetoxy-14-epi-hydroxydolasta-1(15),8-diene, which are detailed in this article.
Type of Medium:
Online Resource
ISSN:
0008-4042
,
1480-3291
Language:
English
Publisher:
Canadian Science Publishing
Publication Date:
2012
detail.hit.zdb_id:
1482256-8
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