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Total Synthesis of (+)‐Pamamycin‐607
Author(s) -
Kang Sung Ho,
Jeong Joon Won,
Hwang Yu Sang,
Lee Sung Bae
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(20020415)41:8<1392::aid-anie1392>3.0.co;2-g
Subject(s) - stereoselectivity , total synthesis , tetrahydrofuran , aldol condensation , epoxide , chemistry , aldol reaction , surface modification , stereochemistry , organic chemistry , catalysis , solvent
Complete stereoselectivity was observed in the total synthesis of pamamycin‐607 ( 1 ), which proceeded by iodoetherification of γ ‐triethylsilyloxyalkenes in the presence of an essential additive, silver carbonate, to provide the requisite three cis ‐2,5‐disubstituted tetrahydrofuran units. Other key functionalization includes cuprate addition to epoxide, olefinations, Paterson aldol condensation, Evans anti reduction, and macrolactonization.