M. Ihara*, F. Setsu, M. Shohda
Sep 1, 1994
Citations
0
Influential Citations
30
Citations
Journal
Journal of Organic Chemistry
Abstract
The radical cyclizations of (±)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)- prop-2-enoates (11) and (12) and (±)-ethyl (E)-3-{N-[2-(bromomethyl)- butyl]-N-[2-(3-indolyl)ethyl]carbamoyl}prop-2-enoate (25) were carried out with (TMS) 3 SiH or Bu 3 SnH in the presence of AIBN. (-)-(2S)-2- ((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cycli- zation of(+)-25 produced piperidinone (18) as a diastereomeric mixture, which was transformed into tacamonine (1)