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  • Title: C-24 stereochemistry of marine sterols: (22E)-24-(isopropenyl)-22-dehydrocholesterol and 24-isopropenylcholesterol.
    Author: Echigo S, Hara N, Carderon GJ, Duque C, Fujimoto Y.
    Journal: Chem Pharm Bull (Tokyo); 2006 Oct; 54(10):1473-7. PubMed ID: 17015996.
    Abstract:
    The C-24 configuration of (22E,24xi)-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 (1)H- and (13)C-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.
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