Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
Stereochemical Studies. XLIX. A Biogenetic-type Total Synthesis of Natural (+)-Maritidine from L-Tyrosine using highly Specific Asymmetric Cyclization
KIYOSHI TOMIOKAKENJI KOGASHUNICHI YAMADA
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Volume 25 (1977) Issue 10 Pages 2681-2688

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Abstract

A first biogenetic-type asymmetric synthesis of natural (+)-maritidine from L-tyrosine is described. Phenolic oxidative coupline of monophenol (10b) with thallium (III) trifluoroacetate afforded the corresponding spiro dienone (11b) in 66.5% yield. Asymmetric cyclization of dienone (14) was found to occur highly selectively to give one diastereomer (15) preferentially. Removal of the carboxamide group in 15 was effected by reductive decyanization of the intermediate amino nitrile (18) by sodium in liquid ammonia to (+)-epimaritidine (19), which was epimerized to the objective (+)-maritidine by the known method.

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