A formal asymmetric synthesis of Calabar bean alkaloids

DOI: 10.1248/cpb.44.715

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 715 - 719 (1996)

Update date:2022-08-17

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Authors:

Node, Manabu

Hao, Xiao-Jiang

Nishide, Kiyoharu

Fuji, Kaoru

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Article abstract of DOI:10.1248/cpb.44.715

A total synthesis of (-)-eserethole (2) has been accomplished using the Diels-Alder reaction of (S)-(-)-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 naturally occurring Calabar bean alkaloids such as (-)-physostigmine (1), (-)- physovenine (17) and (-)-geneserine (18).

Full text of DOI:10.1248/cpb.44.715

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