90925-42-1Relevant articles and documents
Synthesis of (±)-14-epi-hydroxydolasta-1(15),7,9-triene and (±)-7-epi -acetoxy-14-epi-hydroxydolasta-1(15),8-diene
Majetich, George,Yu, Jianhua
, p. 75 - 84 (2012/03/07)
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.