Asymmetric Total Synthesis of (−)‐Cribrostatin 4 (Renieramycin H) | Zendy

Vincent Guillaume | Zendy; Williams Robert M. | Zendy

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Asymmetric Total Synthesis of (−)‐Cribrostatin 4 (Renieramycin H)

Author(s) -

Vincent Guillaume,

Williams Robert M.

Publication year - 2007

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200604126

Subject(s) - tetrahydroisoquinoline , moiety , total synthesis , enantioselective synthesis , tricyclic , lactam , chemistry , stereochemistry , convergent synthesis , pictet–spengler reaction , combinatorial chemistry , organic chemistry , catalysis

Out of the blue : The convergent asymmetric total synthesis of the antitumor antibiotic (−)‐cribrostatin 4 from the blue sponge Cribrochalina features asymmetric Staudinger and Pictet–Spengler reactions to form the tetrahydroisoquinoline moiety. These reactions were followed by a reductive opening/elimination of a tricyclic β‐lactam and a Pictet–Spengler cyclization to access the unsaturated pentacyclic core.

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