19 テルペン系海産天然物の合成研究(口頭発表の部)
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In 1996 stellettadine A (1) was isolated from a marine sponge Stelletta sp. as a metamorphosis-inducing compound for ascidian larvae. Its absolute configuration was proposed as S. The first synthesis of (S)-1 was achieved by starting from (S)-citronellal (4). Although the naturally occurring 1 has been reported to be levorotatory, our synthetic (S)-isomer is dextrorotatory. It suggests that the absolute configuration of natural stellettadine A is not S but R. Naurol A is a cytotoxic metabolite isolated from Pacific sponges, and 2 was proposed as its structure. A mixture of (±)-2 and meso-2' was synthesized from 4-tert-butyldimethylsilyloxy-3-methyl-2-cyclohexen-1-one (10) employing the Stile coupling (12+13→2+2') as the key step. Although our synthetic sample (2+2') was a diastereomeric mixture at C-11, its spectral data (IR, UV, ^1H and ^<13>C NMR and MS etc.) were significantly different from those reported for natural naurol A. It was therefore concluded that the structure 2 proposed for naurol A was in error. In 1997 testudinariol A (3) was isolated from the marine mollusc Pleurobrancus testudinarius. This compound is thought to be defensive allomone of P. testudinarius. We studied the stereoselective synthesis of testudinariol A (3), and we synthesized the key intermediates 28 and 29 by employing intramolecular oxy-Michael addition and ene reaction as the key steps. The conversion of 28 and/or 29 to testudinariol A (3) is now under investigation.
- 天然有機化合物討論会の論文
- 2000-10-01
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