Premium
Novel Strategy for the Synthesis of the Butenolide Moiety of Peridinin
Author(s) -
Olpp Thomas,
Brückner Reinhard
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.200460259
Subject(s) - desymmetrization , butenolide , chemistry , tartaric acid , moiety , stereochemistry , amide , combinatorial chemistry , organic chemistry , enantioselective synthesis , citric acid , catalysis
Tartaric acid is the starting point for the stereoselective synthesis of the butenolide unit (see scheme)in peridinin, a marine carotenoid. Key steps were the desymmetrization of tartaric acid bis(Weinreb amide), an E ‐selective olefination by Ando‐type bromophosphonates, and an anti ‐selective Mitsunobu elimination (for establishing the C 1′ C γ bond).
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom