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Tamosterone Sulfates: A C-14 Epimeric Pair of Polyhydroxylated Sterols from a New Oceanapiid Sponge Genus.
J Org Chem
September 1999
Department of Chemistry and Biochemistry, University of Oklahoma, Norman, Oklahoma 73019, and National Institute of Water and Atmospheric Research (NIWA), Private Bag 109-695, Newmarket, Auckland, New Zealand.
Two novel, C-14 epimeric polyhydroxylated 15-keto steroid sulfates, tamosterone sulfate and 14beta-tamosterone sulfate (1 and 2), were isolated from a sponge belonging to a new genus collected in Yap, Federated States of Micronesia. Their structures were assigned by analysis of spectroscopic data and chemical conversions. 14beta-Tamosterone sulfate (2) has the rare naturally occurring C/D cis ring fusion and is the less stable epimer based on equilibration studies.
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