Synthesis and structural determination of the C33-C42 fragment of symbiodinolide
Synthesis and structural determination of the C33-C42 fragment of symbiodinolide
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DOI：
10.1016/j.tetlet.2008.11.056
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发表时间：
2009-02-25
影响因子：
1.8
通讯作者：
Uemura, Daisuke
中科院分区：
文献类型：
--
作者：
Takamura, Hiroyoshi;Kadonaga, Yuichiro;Uemura, Daisuke
Synibiodinsulate（1）是分子量为2859 μ的多元醇大环内酯。作为降解反应之一，进行作为1的甲酯的2与乙烯的交叉复分解，得到C33-C42降解片段4。用Mosher方法计算了4的绝对构型为（36 S，40 S）。以L-天冬氨酸为起始原料，经14步反应立体选择性地合成了4。合成的双-（S）-和（R）-MTPA酯表现出与衍生自降解片段4的双-（S）-和（R）-MTPA酯相同的光谱数据。因此，4的绝对立体化学被阐明为（36 S，40 S）。(C)2009年由Elsevier Ltd.出版
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.