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Stereoselective Total Synthesis of (−)‐Borrelidin
Author(s) -
Vong Binh G.,
Kim Sun Hee,
Abraham Sunny,
Theodorakis Emmanuel A.
Publication year - 2004
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.200460203
Subject(s) - regioselectivity , retrosynthetic analysis , alkyne , stereoselectivity , stereochemistry , chemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis
A convergent synthesis of (−)‐borrelidin ( 1 ) is reported based on the retrosynthetic disconnections indicated in the picture. Highlights of the strategy include the construction of a strained enynone‐containing macrolide and the installation of a cyano group in a regioselective manner by a novel molybdenum‐catalyzed hydrostannation of the alkyne.