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Total Synthesis of Cruentaren A
Author(s) -
Vintonyak Viktor V.,
Maier Martin E.
Publication year - 2007
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.200701423
Subject(s) - triple bond , ether , ring (chemistry) , chemistry , cleavage (geology) , stereochemistry , combinatorial chemistry , computer science , double bond , organic chemistry , engineering , fracture (geology) , geotechnical engineering
A triple bypass : The triple bond in the macrolactone ring of 2 served as a lock to prevent the unwanted translactonization to the δ‐lactone during the formation of the side chain of the macrolide cruentaren A ( 1 ). Subsequent cleavage of the methyl ether and the silicon protecting groups (PG) followed by a Lindlar reduction of the two triple bonds completed the synthesis (see scheme).