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Total Synthesis of (+)‐Dactylolide through an Efficient Sequential Peterson Olefination and Prins Cyclization Reaction
Author(s) -
Aubele Danielle L.,
Wan Shuangyi,
Floreancig Paul E.
Publication year - 2005
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.200500564
Subject(s) - prins reaction , chemistry , allylic rearrangement , enantioselective synthesis , acetal , key (lock) , total synthesis , natural product , product (mathematics) , stereochemistry , computer science , organic chemistry , mathematics , catalysis , operating system , geometry
Key steps in the total synthesis of the macrolide natural product (+)‐dactylolide (see formula) include two enantioselective vinylogous Mukaiyama reactions, fragment coupling through acetal formation, a sequential Peterson olefination/Prins cyclization reaction that proceeds under very mild conditions, and a Mislow–Evans rearrangement to effect the transposition of an allylic alcohol.
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