133709-58-7Relevant articles and documents
Compactin from Hajos (-)-enedione
Daniewski, A. R.,Uskokovic, M. R.
, p. 849 - 856 (2007/10/02)
The hexahydronaphthalene portion of compactin was synthesized from the easily accessible (-)-enedione 8.Reductive alkylation employing tert-butyl copper hydride and 4-(tert-butyldimethylsilyloxy)-butanal leads to the epimeric acetates 10 and 14 in a ratio of 2:1.Both of them have been converted to a more advanced intermediate, the diacetate 21, which was transformed to 29 by dehydration, hydrogenation and allylic hydroxylation.Dehydration of 29 with Martin reagent has produced preferentially the desired diene 31, from which the target molecule 7 was obtained by partial hydrolysis.