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Highly Efficient Stereocontrolled Total Synthesis of the Polyfunctional Carotenoid Peridinin
Author(s) -
Furuichi Noriyuki,
Hara Hirokazu,
Osaki Takashi,
Mori Hajime,
Katsumura Shigeo
Publication year - 2002
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 - 10.1002/1521-3773(20020315)41:6<1023::aid-anie1023>3.0.co;2-a
Subject(s) - chemistry , carotenoid , peridinin , wittig reaction , reagent , stereoselectivity , total synthesis , butenolide , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , fucoxanthin
The convergent, highly stereoselective synthesis of the nor carotenoid peridinin ( 1 ) is based on the following key steps: a) a Sharpless asymmetric epoxidation, b) reaction with a silylfuran‐Wittig reagent and oxidation with 1 O 2 , c) a Pd‐catalyzed three‐step one‐pot procedure for the formation of the ylidene butenolide segment), and d) a modified Julia olefination. This provides a new method for the synthesis of carotenoids.