179554-12-2

Upstream product

• 39053-43-5 1-bromo-2,4-dimethyl-3-nitro-benzene 
• 81-20-9 2,6-dimethylnitrobenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1260743-46-1 2-(bromomethyl)-4-methoxy-1,3-dimethylbenzene 
• 1354972-38-5 3-ethoxy-2-isopropyl-5-(3-methoxy-2,6-dimethylbenzyl)-5-methylcyclopent-2-en-1-one 
• 1354972-34-1 2-isopropyl-4-(3-methoxy-2,6-dimethylbenzyl)-4-methyl-3-vinylcyclopent-2-en-1-one 
• 90925-42-1 (3-methoxy-2,6-dimethylphenyl)methanol 

Relevant academic research and scientific papers

Synthesis of (±)-14-epi-hydroxydolasta-1(15),7,9-triene and (±)-7-epi -acetoxy-14-epi-hydroxydolasta-1(15),8-diene

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.