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Total Synthesis of Cyanolide A in the Absence of Protecting Groups, Chiral Auxiliaries, or Premetalated Carbon Nucleophiles
Author(s) -
Waldeck Andrew R.,
Krische Michael J.
Publication year - 2013
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.201300843
Subject(s) - nucleophile , chemistry , carbon fibers , total synthesis , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , materials science , composite number , composite material
No protection, no problem : The C 2 ‐symmetric macrodiolide cyanolide A is prepared in six steps from neopentyl glycol and allyl acetate by iridium‐catalyzed double asymmetric allylation and a tandem cross‐metathesis/oxa‐Michael cyclization to form the substituted pyran. The synthesis is accomplished in the absence of any protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles in fewer than half the steps of any prior approach.