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Stereoselective Total Synthesis of (+)‐Norrisolide
Author(s) -
Brady Thomas P.,
Kim Sun Hee,
Wen Ke,
Theodorakis Emmanuel A.
Publication year - 2004
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.200352868
Subject(s) - stereoselectivity , lactol , total synthesis , stereochemistry , natural product , bicyclic molecule , chemistry , lactone , ring (chemistry) , combinatorial chemistry , computer science , organic chemistry , catalysis
In a convergent approach to the marine natural product (+)‐norrisolide ( 1 ) the two bicyclic ring systems are coupled through the C9C10 bond to assemble the carbon framework in a late stage of the synthesis. Other highlights of the synthetic strategy include the formation of the unusual fused γ‐lactone–γ‐lactol motif of 1 through a sequence of oxidation reactions.