Divergent Synthesis of Nerolidol-type Sesquiterpenoids Produced by Soil Bacterium from an Identical Starting Material via Diepoxide Precursors: Stereochemical Revision and Absolute Configuration of a THF Natural Product

Abstract

A divergent asymmetric synthesis of two nerolidol-type sesquiterpenoids with a five- or a six-membered ether ring was established from an identical commercially available trans,trans-farnesyl acetate through the cyclization of diepoxide precursors under simple acidic or neutral conditions, respectively. In addition, the relative configuration of a nerolidol-type sesquiterpenoid with a tetrahydrofuran ring was revised. Its absolute configuration was determined by its asymmetric synthesis and a modified Mosher’s analysis. Furthermore, the cytotoxicity and nitric oxide production inhibitory activity of the synthesized compounds were assessed.

Divergent synthesis, Stereochemical revision, Absolute configuration