Marine Terpenes and Terpenoids: VII: Minor Cembranoid Derivatives, Structurally Related to the Potent Anti-tumor-Promoter Sarcophytol A, from the Soft Coral Sarcophyton glaucum

Abstract

Eight new cembranoids, sarcophytol M (3), sarcophytol N (9a), sarcophytol J (11a), sarcophytol H and its diacetate (15a and 15b), sarcophytol O (18), sarcophytol I (19a) and sarcophytol G (24a), and known cembranoids nephthenol (7) and sinulariol D (8), were isolated from the soft coral Sarcophyton glaucum. Their structures were determined from the spectroscopic properties and by chemical conversion. Sarcophytol M (3) was found to be the enantiomer of the known compound cembrenol from a terrestrial plant. Sarcophytol N (9a) and sarcophytol J (11a) were the geometrical isomers at C-3 of the major components sarcophytol A (la) and sarcophytol B (2a), which are potent anti-tumor-promoters. Sarcophytol H and sarcophytol O were identical with the diols 15a and 18, respectively, which were previously synthesized from la. Sarcophytol I (19a) and sarcophytol G (24a) were the diastereoisomers of the known compounds sarcophytol E (22a) and sarcophytol D (21), respectively, and their absolute configurations were determined by chemical conversion of two 11,12£-epoxides (20 and 23). © 1989, The Pharmaceutical Society of Japan. All rights reserved.