Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product. Issue 44 (4th November 2015)

• Record Type: Journal Article
• Authors: Ishigami, Ken; Kobayashi, Munetaka; Takagi, Motoki; Shin-ya, Kazuo; Watanabe, Hidenori
• Is Part Of: Tetrahedron. Volume 71:Issue 44(2015)
• Page Start: 8436
• Page End: 8443
• Publication Date: 2015-11-04
• Subjects: Topsentolide A1 -- 9-Membered lactone -- Determination of the absolute configuration -- Marine oxylipin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.09.013
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Four possible stereoisomers of topsentolide A1, a cytotoxic oxylipin against human solid tumor cell lines, were efficiently synthesized in a stereoselective manner in order to determine the stereochemistry of natural product. The absolute configuration of topsentolide A1 was determined to be 8 R, 11 R, 12 S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product. Cytotoxicity of the synthetic isomers was also examined. Graphical abstract: