Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis.

ABSTRACT: Many natural products contain a C = C double bond through which various other derivatives can be prepared; the stereochemical identity of the alkene can be critical to the biological activities of such molecules. Catalytic ring-closing metathesis (RCM) is a widely used method for the synthesis of large unsaturated rings; however, cyclizations often proceed without control of alkene stereochemistry. This shortcoming is particularly costly when the cyclization reaction is performed after a long sequence of other chemical transformations. Here we outline a reliable, practical and general approach for the efficient and highly stereoselective synthesis of macrocyclic alkenes by catalytic RCM; transformations deliver up to 97% of the Z isomer owing to control induced by a tungsten-based alkylide

SUBMITTER: Yu M 

PROVIDER: S-EPMC3211109 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature