Total Synthesis of Chlorinated Oxylipin Eiseniachloride B

Abstract

Eiseniachloride B is a marine chlorinated oxylipin isolated from the brown alga Eisenia bicyclis. This natural product contains cyclopentane, chlorohydrin, and 14-membered lactone systems that incorporate five stereogenic centers. In this paper, we report on the total synthesis of structurally unique oxylipin eiseniachloride B from optically active lactol via ecklonialactone B in a linear sequence comprising 11 steps with a 12.1% overall yield.

Keywords: chlorinated oxylipin; ecklonialactone B; eiseniachloride B; face-selective epoxidation; macrolactone; total synthesis.