Enantioselective Construction of the ABCDE Pentacyclic Core of the Strychnos Alkaloids | Zendy

Adam D. Gammack Yamagata | Zendy; Darren J. Dixon | Zendy

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Enantioselective Construction of the ABCDE Pentacyclic Core of the Strychnos Alkaloids

Author(s) -

Adam D. Gammack Yamagata,

Darren J. Dixon

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b00669

Subject(s) - enantioselective synthesis , chemistry , stereocenter , strychnos , moiety , desymmetrization , stereochemistry , ring (chemistry) , indole test , amine gas treating , combinatorial chemistry , organic chemistry , alkaloid , catalysis

An efficient enantioselective 12-step synthesis of the ABCDE pentacyclic core of the Strychnos alkaloids is described. A key feature of this approach is an organocatalyzed enantioselective desymmetrization to generate the morphan core in high ee and dr. After palladium-catalyzed installation of the indole moiety, a subsequent 5-exo-trig dearomatizing atom transfer radical cyclization was developed to construct the C-ring. Following a series of functional group interconversions, the pentacyclic amine core was obtained with all the relevant architecture including five stereocenters pertaining to the Strychnos alkaloids.

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