A novel four-step synthetic route to enantiopure cyclopentene carboxylic ac
ids starting from commercially available 3-endo-bromocamphor is described.
The synthesis is straightforward and practical. The key transformations inv
olve firstly, an enantiospecific Wagner-Meerwein rearrangement of a bromoca
mphor derived cyanohydrin, and secondly the regiospecific C-(1) C-(2) bond
scission of a 7-bromonorbornan-3-one. (C) 2001 Elsevier Science Ltd. All ri
ghts reserved.