Chirality Transfer and Asymmetric Catalysis: Two Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine

Two strategies are described en route to an enantioselective total synthesis of gelsenicine. One approach centers on a chirality transfer cycloisomerization that ultimately fell short. Separately, an asymmetric catalysis route utilizing bisphosphine-gold-catalyzed cycloisomerization was pursued. A c...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 27; pp. 4971 - 4976
Main Authors Knutson, Phil C., Ji, Haofan, Harrington, Christopher M., Ke, Yan-Ting, Ferreira, Eric M.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 15.07.2022
Subjects
Catalysis
Indole Alkaloids
Molecular Structure
Stereoisomerism
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Summary:Two strategies are described en route to an enantioselective total synthesis of gelsenicine. One approach centers on a chirality transfer cycloisomerization that ultimately fell short. Separately, an asymmetric catalysis route utilizing bisphosphine-gold-catalyzed cycloisomerization was pursued. A catalytic system was identified that provided a synthetic intermediate in our Gelsemium alkaloid syntheses in high enantiopurity and with absolute configuration determined by electronic circular dichroism, thus representing an enantioselective formal total synthesis of (+)-gelsenicine.
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P.C.K. and H.J. contributed equally.
Author Contributions
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01974