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Communication | Special issue | Vol 37, No. 1, 1994, pp.289-292
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S132
A Total Synthesis of (±)-Tacamonine (Pseudovincamone I) through Radical Cyclization

Masataka Ihara, Fumihito Setsu, Miyuki Shohda, Nobuaki Taniguchi, and Keiichiro Fukumoto:

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The radical cyclization of the bromo ester (11), prepared from 2-hydroxymethylbutan-1-ol (7), giving the diastereoisomeric mixture of lactones (12) was examined under various conditions. Treatment of the bromo ester (17), derived from 7, with tris(trimethylsilyl)silane in the presence of 2,2-azoisobutyronitrile provided the epimeric mixture of lactams (18), convertible to (±)-tacamonine (pseudovincamone I) (1) in three steps.