52 生物活性を有する海産テルペノイドAplidiasphingosineの合成研究

概要

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Aplidiasphingosine (1, 2-amino-5,9,13,17-tetramethyl-8,16-octadecadiene-1,3,14-triol) is an antimicrobial and antitumor terpenoid isolated from an Aplidium sp. (marine tunicate). The presence of five chiral centers in 1 demands 32 stereoisomers. However, nothing was known concerning its stereochemistry with no available chiroptical data. In order to determine the relative stereochemistry of 1, its (±)-2,3-erythro isomer, 1a, and (±)-2,3-threo isomer, 1b, were synthesized, and 2,3-threo and 13,14-erythro relative configurations were proposed for 1 by examining their <13>^C-NMR spectra. Subsequently, D-erythro-dihydrosphingosine triacetate 17c and (2S,3S,5R)-2-acetamino-5,9-dimethyl-8-decene-1,3-diol 22b were synthesized by employing the Sharpless asymmetric epoxidation as a key reaction. And, <13>^C-NMR study of 22b coupled with biogenetic consideration enabled us to propose (2S,3S,5S,13R,14S)-stereo-chemistry for 1.
天然有機化合物討論会の論文
1981-09-10