Issue 4, 1991

Synthetic approaches to the naphthyl-isoquinoline alkaloids. Part 2. The total synthesis of (–)-O-methylancistrocladine and (+)-O-methylhamatine and their enantiomers

Abstract

An asymmetric total synthesis of the naphthyl-isoquinoline alkaloids (–)-O-methytancistrocladine 39 is described; the synthetic method also provides routes to the atropisomer (+)-O-methylhamatine 43 and the enantiomers of these alkaloids. The asymmetric construction of the biaryl linkage involved the reaction of the Grignard reagent derived from 2-(2-bromo-3,5-dimethoxyphenyl)-1,3-dioxane 7 with (+)-(4S,5S)-4-(methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydrooxazole 5.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 845-854

Synthetic approaches to the naphthyl-isoquinoline alkaloids. Part 2. The total synthesis of (–)-O-methylancistrocladine and (+)-O-methylhamatine and their enantiomers

M. A. Rizzacasa and M. V. Sargent, J. Chem. Soc., Perkin Trans. 1, 1991, 845 DOI: 10.1039/P19910000845

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