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A Concise Total Synthesis of (+)-Heliotridine

✍ Scribed by Federica Pisaneschi; Franca M. Cordero; Alberto Brandi

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
91 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A practical synthesis of the necine base (+)‐heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3‐dipolar cycloaddition of (S)‐3‐tert‐butoxypyrroline N‐oxide (2) to the commercially available ethyl 4‐bromocrotonate, followed by a suitable elaboration of the adduct. The synthesis gives a 17% overall yield from nitrone 2. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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