Premium
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.