- 著者
- 杉山 重夫 本田 昌徳 古森 徹哉
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- vol.31, pp.22-29, 1989
In our study on the isolation and structure elucidation of biologically active compounds from marine invertebrates, we synthesized the four diastereomers of C_<16>-phytosphingosine (10, 12, 25, and 26), acanthacerebroside A (1), and D-galactosylceramide (3b) as described below. (2S, 3S)-Allylic alcohol, which was prepared from the L-serine derivative and the (E)-vinylalane compound, was converted into (2S, 3S, 4R)- and (2S, 3S, 4S)-phytosphingosines by epoxidation, DIBAH reduction, and debenzylation. The same treatment of (2S, 3R)-allylic alcohol gave (2S, 3R, 4R)- and (2S, 3R, 4S)-phytosphingosines. (2R)-Acetoxytetracosanoic acid was prepared and coupled to (2S, 3S, 4R)-phytosphingosine to give the ceramide (34). Glycosylation of 34 gave the desired monoglycoside (36) and the bisglycoside (37). 36 was converted into 1 by deacetylation. New D-galactosylceramides were isolated from Chondropsis sp., but the absolute stereochemistry has not been determined. Therefore, (2S, 3S, 4R, 6E)- and (2R, 3R, 4R, 6E)-phytosphingosines were prepared via asymmetric epoxidation. The former was transformed to (2S, 3S, 4R, 6E, 2'R)-D-galactosylceramide and its heptaacetate. The spectral data of them were in excellent agreement with those of the natural specimens.
- 著者
- 本田 昌徳 上田 義隆 杉山 重夫 古森 徹哉
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.39, no.6, pp.1385-1391, 1991-06-25 (Released:2008-03-31)
- 参考文献数
- 24
- 被引用文献数
- 12 20
A cerebroside, 1-O-(β-D-galactopyranosyloxy)-(2S, 3S, 4R, 6E)-2-[(R)-2-hydroxytetracosanoylamino]-17-methyl-6-octadecene-3, 4-diol (2), was asymmetrically synthesized from isobutyraldehyde. On the basis of a comparison of the physical data, the absolute structure of a new cerebroside 1b from a Chondropsis sp. sponge is thought to be the same at that of 2.