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Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy
Author(s) -
Trost Barry M.,
Sieber Joshua D.,
Qian Wei,
Dhawan Rajiv,
Ball Zachary T.
Publication year - 2009
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.200901907
Subject(s) - alkyne , moiety , electrophile , nucleophile , total synthesis , retrosynthetic analysis , chemistry , triple bond , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , double bond
A triple‐bond bonanza : The alkyne functional group can be a valuable handle for organic synthesis because the alkyne unit can function both as a nucleophile or as an electrophile when activated with an appropriate metal catalyst. This dual nature of the alkyne moiety has been exploitated for the concise total synthesis of the natural product soraphen A (see retrosynthesis; PMB= para ‐methoxybenzyl, TBS= tert ‐butyldimethylsilyl).