Total synthesis and complete assignment of the stereostructure of a cytotoxic bromotriterpene polyether (+)-aurilol
Total synthesis and complete assignment of the stereostructure of a cytotoxic bromotriterpene polyether (+)-aurilol
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DOI：
10.1021/ja050123p
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发表时间：
2005-04-27
影响因子：
15
通讯作者：
Takaishi, M
中科院分区：
文献类型：
--
作者：
Morimoto, Y;Nishikawa, Y;Takaishi, M
The plane structure and partial stereochemistry of a cytotoxic bromotriterpene polyether (+)-aurilol (1), isolated from the sea hareDolabella auricularia, were mainly elucidated by NMR methods; however, determination of the entire stereochemistry has not been reached. Although there have also been many other types of triterpene polyethers, it is often difficult to determine their stereostructures even by the current highly advanced spectroscopic methods, especially in acyclic systems including quaternary carbon centers such as C10−C11, C14−C15, and C18−C19 in1. In this paper, we report that the total assignment of the incomplete stereostructure of (+)-aurilol (1) to the structural formula2has been accomplished through its first asymmetric total synthesis featuring the highly regio- and stereocontrolled biogenetic-like A−D ether ring formations.
