Journal
TETRAHEDRON LETTERS
Volume 50, Issue 8, Pages 863-866Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.11.056
Keywords
Polyol macrolide; Symbiodinolide; Absolute configuration; Cross-metathesis degradation; Chemical synthesis
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Funding
- Okayama Foundation for Science and Technology
- Naito Foundation
- MEXT, Japan
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Synibiodinolide (1) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2, which is a methyl ester of 1, with ethylene was performed to give the C33-C42 degraded fragment 4. The absolute configuration of 4 was estimated to be (36S,40S) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from L-aspartic acid. Synthetic bis-(S)-and (R)-MTPA esters exhibited the spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded fragment 4. Thus, the absolute stereochemistry of 4 was elucidated to be (36S,40S). (C) 2009 Published by Elsevier Ltd.
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