131833-56-2Relevant academic research and scientific papers
1,3-Elimination Reactions of (3,4-Epoxybutyl)stannanes. Approach to the Synthesis of Hirsutene
Plamondon, Louis,Wuest, James D.
, p. 2076 - 2081 (2007/10/02)
An advanced tricyclic precursor of hirsutene (3) was prepared by a 1,3-elimination reaction of spirocyclic epoxy stannane (7b).Compound 7b was synthesized efficiently from hydroxycyclohexenone 8b by conjugate addition of 2CuLi, Wittig methylenation, and VO(acac)2-catalyzed epoxidation.Intermediate 8b was prepared in five steps from the known enone 9 in 18percent overall yield.An improved synthesis makes compound 9 available in four efficient steps from keto ester 12.
