A New Approach to the Synthesis of Chiral Blocks for Cyclopentanoids

Abstract

A microreview is presented of the development by the authors of the original preparation of enantiomerically pure cyclopentane blocks from the racemic [2+2]-cycloadducts of 1,3-cyclopentadiene and its derivatives with dichloroketene.

Development of a new approach for the synthesis of (+)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester based on the [2+2]-cycloadduct of 5-trimethylsilylcyclopentadiene and dichloroketene

“…13 In the course of further studies, based on the obtained chiral bicyclic lactones, both total (sarcomycin A methyl ester, 14 cyclosarcomycin, 15 homocyclosarcomin, 6,12 entecavir, 17 and didesmethylmethylenomy-cin A methyl ester 18 ) and formal (brefeldin A, analogues of spinosyn A, and iso-and neuroprostanes 19 ) syntheses of a number of biologically active cyclopentanoids were developed. 20 Enantiomers 6 attracted our attention when we were considering the possibilities of using the obtained results in the synthesis of prostanoids. The reason was the presence of an allylsilane moiety, which can be transformed into an allylic alcohol by sequential epoxidation/Peterson-type fragmentation reactions.…”

“…13 In the course of further studies, based on the obtained chiral bicyclic lactones, both total (sarcomycin A methyl ester, 14 cyclosarcomycin, 15 homocyclosarcomin, 6,12 entecavir, 17 and didesmethylmethylenomy-cin A methyl ester 18 ) and formal (brefeldin A, analogues of spinosyn A, and iso- and neuroprostanes 19 ) syntheses of a number of biologically active cyclopentanoids were developed. 20…”

New chiral block for cyclopentanoids synthesis

“…For syntheses of natural cyclopentanoids and their analogs chiral functionalized derivatives of cyclopentane [1][2][3][4][5] are required. In the approach we are developing to carbacyclin 1 [6] and its analogues we have chosen as the initial compound trisubstituted chiral bicyclic lactone 2 (Scheme 1).…”