Total synthesis and complete assignment of the stereostructure of a cytotoxic bromotriterpene polyether (+)-aurilol.
The plane structure and partial stereochemistry of a cytotoxic bromotriterpene polyether (+)-aurilol (1), isolated from the sea hare Dolabella 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 in 1. In this paper, we report that the total assignment of the incomplete stereostructure of (+)-aurilol (1) to the structural formula 2 has been accomplished through its first asymmetric total synthesis featuring the highly regio- and stereocontrolled biogenetic-like A-D ether ring formations.
Morimoto
Yoshiki
Y
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp
Nishikawa
Yoshihiro
Y
Takaishi
Mamoru
M
D000818:Animals; D001048:Aplysia / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis*
D004987:Ethers; D004988:Ethers, Cyclic; D006842:Hydrocarbons, Brominated; D013729:Terpenes; D014315:Triterpenes; C502249:aurilol