Silicon-Based Cross-Coupling Reactions in the Total Synthesis of Natural Products

Unlike other variants of transition-metal-catalyzed cross-coupling reactions, those based on organosilicon donors have not been used extensively in natural product synthesis. However, recent advances such as: 1) the development of mild reaction conditions, 2) the expansion of substrate scope, 3) the...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2010-04, Vol.49 (17), p.2978-2986
Main Authors: Denmark, Scott E, Liu, Jack H.-C
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
cross-coupling
organopalladium
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
organosilicon reagents
silanols
tandem reactions
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Unlike other variants of transition-metal-catalyzed cross-coupling reactions, those based on organosilicon donors have not been used extensively in natural product synthesis. However, recent advances such as: 1) the development of mild reaction conditions, 2) the expansion of substrate scope, 3) the development of methods to stereoselectively and efficiently introduce the silicon-containing moiety, 4) the development of a large number of sequential processes, and 5) the advent of bifunctional bis(silyl) linchpin reagents, signify the coming of age of silicon-based cross-coupling reactions. The following case studies illustrate how silicon-based cross-coupling reactions play a strategic role in constructing carbon-carbon bonds in selected target molecules.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200905657