Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Lupin Alkaloids. IV. Total Syntheses of Optically Active Matrine and Allomatrine
Shigenobu OkudaMasafumi YoshimotoKyosuke Tsuda
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1966 Volume 14 Issue 3 Pages 275-279

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Abstract
Didehydromatrine (III) was reduced to (±)-allomatrinol (VI') and (±)-matrinol (VII'), and the latter of which was converted to N-benzoyl derivative (VIII'). The optical resolution of VI' and VIII' were carried out by means of dibenzoyl-(+)-tartaric acid. N-Benzoyl-(+)-matrinol (VIII) was transformed to (+)-matrinol (VII) via hydrogenolysis. (+)-Matrinol (VII) and (+)-allomatrinol (VI) were derived into (+)-matrine (I) and (+)-allomatrine (V) by oxidation and successive cyclization.
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© The Pharmaceutical Society of Japan
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