Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids

Abstract

Assignment of configuration to the 1,10-double bond in the cis-trans isomeric 3β-acetoxy-5,10-seco-1,10-cholesten-5-ones has been achieved by means of NMR spectrometry. Some reactions of these new compounds have been studied and, as expected from conformational analysis, it was found that only the trans-isomer readily undergoes transannular cyclizations