期刊
TETRAHEDRON
卷 65, 期 36, 页码 7449-7456出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.07.019
关键词
Symbiodinolide; Absolute configuration; Cross-metathesis degradation; Chemical synthesis
资金
- Okayama Foundation for Science and Technology
- NOVARTIS Foundation (Japan) for the Promotion of Science
- Mitsubishi Foundation
- Japan Society for the Promotion of Science [19710184, 21710231, 16GS0206]
- Grants-in-Aid for Scientific Research [19710184, 21710231] Funding Source: KAKEN
Cross-metathesis of methyl ester which was prepared from symbiodinolide with ethylene was performed to give the C33-C42 degraded fragment. This fragment was estimated to be (36S,40S)-diol by the modified Mosher method. Stereoselective synthesis of the (36S,40S)-diol and its diastereomer (36R,40S)-diol was achieved from L-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters which were derivatized from the (36S,40S)-diol exhibited spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded product. Thus, the absolute stereochemistry of the C33-C42 fragment was elucidated to be (36S,40S). (C) 2009 Elsevier Ltd. All rights reserved.
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