Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta, 10alpha-epoxy-salonitenolide
- Authors: Rosselli, S; Maggio, AM; Raccuglia, RA; Morris-Natschke, SL; Bastow, KF; Lee, KH; Bruno, M
- Publication year: 2010
- Type: Articolo in rivista (Articolo in rivista)
- Key words: germacranolides, epoxygermacranolides, cyclization, eudesmanolides, absolute configuration, cytotoxicity
- OA Link: http://hdl.handle.net/10447/54918
Abstract
The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.