Formal Synthesis of (-)-Haliclonin A: Stereoselective Construction of an Azabicyclo[3.3.1]nonane Ring System by a Tandem Radical Reaction.

Keita Komine,Yasuhiro Urayama,T. Hosaka,Yuki Yamashita,H. Fukuda,S. Hatakeyama,Jun Ishihara

Published 2020 in Organic Letters

ABSTRACT

A formal synthesis of (-)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the highly stereoselective tandem radical reaction to construct the azabicyclo[3.3.1]nonane core and the enantioselective formation of an all-carbon quaternary center via the Pd-mediated deracemization.

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