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

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-carbo...

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Bibliographic Details
Published in:Organic letters 2020-07, Vol.22 (13), p.5046-5050
Main Authors: Komine, Keita, Urayama, Yasuhiro, Hosaka, Taku, Yamashita, Yuki, Fukuda, Hayato, Hatakeyama, Susumi, Ishihara, Jun
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01627