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Total Synthesis of (-)-Haploscleridamine

Author:
Singha Roy, Moumita, Meng, Xiaofeng, Koda, Karuna, Rasapalli, Sivappa, Gout, Delphine, Lovely, Carl J.
Source:
Tetrahedron letters 2019
ISSN:
0040-4039
Subject:
alcohols, alkaloids, chemical reactions, histidine, moieties
Abstract:
Asymmetric total synthesis of the imidazole containing β–carboline natural product, haploscleridamine, from histidine is described. Key to the successful assembly of this alkaloid is a ring-closing metathesis reaction of an imidazole derived allylic alcohol to construct a 3-piperidinone. Application of the Buchwald-modification of the classical Fischer indolization and deprotection of the N-tosyl moiety delivered haploscleridamine.
Agid:
6328790