C-24 Stereochemistry of Marine Sterols: (22E)-24-(Isopropenyl)-22-dehydrocholesterol and 24-Isopropenylcholesterol

Abstract

The C-24 configuration of (22E,24ξ)-24-isopropenyl-22-dehydrocholesterol (1), which was recently isolated from the Colombian Caribbean sponge, Topsentia ophiraphidites, was investigated. Synthesis of the stereodefined (24R)- and (24S)-(22E)-24-isopropenyl-22-dehydrocholesterols (1a, 1b) followed by ¹H- and ¹³C-NMR data comparison of these sterols established the (24R)-configuration of 1. In addition, (24R)- and (24S)-24-isopropenylcholesterols (2a and 2b) were also synthesized and their NMR data are provided. The C-24 configurations of the samples of 24-isopropenylcholesterol reported previously are discussed.