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Gold(I)‐Catalyzed Cyclizations of Silyl Enol Ethers: Application to the Synthesis of (+)‐Lycopladine A
Author(s) -
Staben Steven T.,
KennedySmith Joshua J.,
Huang David,
Corkey Britton K.,
LaLonde Rebecca L.,
Toste F. Dean
Publication year - 2006
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.200602035
Subject(s) - silylation , enol , chemistry , intramolecular force , reactivity (psychology) , catalysis , double bond , enol ether , silyl ether , organic chemistry , medicine , alternative medicine , pathology
In control : Gold(I)‐catalyzed intramolecular addition of silyl enol ethers to alkynes and allenes allows for the diastereoselective synthesis of cyclopentenes with control of the position of the double bond. The utility of these reactions is demonstrated by an efficient total synthesis of (+)‐lycopladine A that takes advantage of the orthogonal reactivity of Au I and Pd 0 towards unsaturated iodides (see scheme).