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 inOrganic letters Vol. 22; no. 13; pp. 5046 - 5050
Main Authors Komine, Keita, Urayama, Yasuhiro, Hosaka, Taku, Yamashita, Yuki, Fukuda, Hayato, Hatakeyama, Susumi, Ishihara, Jun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
HALICLONIN
ENANTIOSELECTIVE SYNTHESIS
REDUCTION
ESTERS
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01627