Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
A Formal Asymmetric Synthesis of Calabar Bean Alkaloids
Manabu NODE, Xiao-jiang HAO, Kiyoharu NISHIDE, Kaoru FUJI
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Keywords: (-)-eserethole, (-)-physostigmine, symmetric nitroolefination, Diels-Alder reaction, nitro group, aromatization
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1996 Volume 44 Issue 4 Pages 715-719

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Abstract
A total synthesis of (-)-eserethole (2) has been accomplished using the Diels-Alder reaction of (S)-(-)-2-methyl-2-[2-(E)-nitroethenyl]-δ-valerolactone (3) and Danishefsky's diene as a key step. The synthesis of optically pure (-)-eserethole (2) constitutes a formal synthesis of naturaly occurring Calabar bean alkaloids, such as (-)-physostigmine (1), (-)-physovenine (17) and (-)-geneserine (18).
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© The Pharmaceutical Society of Japan
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