A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-TACAMONINE (PSEUDOVINCAMONE-I) THROUGH RADICAL CYCLIZATION

Authors
IHARA M SETSU F SHOHDA M TANIGUCHI N FUKUMOTO K
Citation
M. Ihara et al., A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-TACAMONINE (PSEUDOVINCAMONE-I) THROUGH RADICAL CYCLIZATION, Heterocycles, 37(1), 1994, pp. 289-292
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
37
Issue
1
Year of publication
1994
Pages
289 - 292
Database
ISI
SICI code
0385-5414(1994)37:1<289:ATSO((>2.0.ZU;2-9
Abstract
The radical cyclization of the bromo ester (11), prepared from 2-hydro xymethylbutan-1-ol (7), giving the diastereoisomeric mixture of lacton es (12) was examined under various conditions. Treatment of the bromo ester (17), derived from 7, with tris(trimethylsilyl)silane in the pre sence of 2,2-azoisobutyronitrile provided the epimeric mixture of lact ams (18), convertible to (+/-)-tacamonine (pseudovincamone I) (1) in t hree steps.