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Total Synthesis of (–)‐Epothilone B: An Extension of the Suzuki Coupling Method and Insights into Structure–Activity Relationships of the Epothilones
Author(s) -
Su DaiShi,
Meng Dongfang,
Bertinato Peter,
Balog Aaron,
Sorensen Erik J.,
Danishefsky Samuel J.,
Zheng YuHuang,
Chou TingChao,
He Lifeng,
Horwitz Susan B.
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199707571
Subject(s) - epothilones , dimethyldioxirane , epothilone , suzuki reaction , chemistry , natural product , stereochemistry , stereoselectivity , total synthesis , derivative (finance) , combinatorial chemistry , organic chemistry , aryl , financial economics , economics , catalysis , alkyl
The highest biological activities displayed by epothilone‐related compounds have been found for epothilone B ( 1 ) and a derivative that was prepared en route to the natural product. Key steps in the total synthesis were a Suzuki coupling providing a trisubstituted double bond in the macrocycle and its subsequent stereoselective epoxidation with dimethyldioxirane.