C-24 stereochemistry of marine sterols: (22E)-24-(isopropenyl)-22-dehydrocholesterol and 24-isopropenylcholesterol |
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| Authors: | Echigo Shizue Hara Noriyuki Carderon Gladys Jeanette Duque Carmenza Fujimoto Yoshinori |
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| Institution: | Department of Chemistry and Materials Science, Tokyo Institute of Technology, Tokyo, Japan. |
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| 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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