Synthesis of Enantiomerically Pure Cyclopentene Building Blocks
07 February 2007 (online)
An efficient synthesis of the enantiomerically pure cis-annulated cyclopentenes 2 and ent-2 was established by the use of an enzymatic transesterification and hydrolysis, respectively, followed by an SN2-type substitution with a benzyloxymethyl cuprate and a sigmatropic rearrangement. The advantage of this approach is the short sequence combined with an excellent overall yield and an enantiomeric excess of 99%.
cyclopentenes - enzymes - benzyloxymethyl cuprate - spinosyns - Claisen-Ireland rearrangement