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Total Synthesis of (−)‐atrop‐Abyssomicin C
Author(s) -
Bihelovic Filip,
Saicic Radomir N.
Publication year - 2012
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.201108223
Subject(s) - enantioselective synthesis , ring (chemistry) , cyclohexane , stereochemistry , sequence (biology) , chemistry , catalysis , combinatorial chemistry , total synthesis , dual (grammatical number) , organic chemistry , philosophy , biochemistry , linguistics
Rolling in the deep : An enantioselective synthesis of a marine antibiotic (−)‐atrop‐abyssomicin C (see scheme) is described. The key steps of the synthetic sequence are the application of dual catalysis in the formation of the cyclohexane core, the gold‐catalyzed formation of a tricyclic spirotetronate unit, and a highly efficient eleven‐membered ring closure by a Nozaki–Hiyama–Kishi reaction.