Total Synthesis of (+)-7-epi-Tarchonanthuslactone via a Chelation-Controlled Mukaiyama Aldol Reaction

Abstract

An asymmetric total synthesis of (+)-7-epi-tarchonanthuslactone was achieved from commercially available methyl (R)-3-hydroxybutyrate. The key step employed a diastereoselective chelation-controlled Mukaiyama aldol reaction to construct the chiral hydroxyl group at the C-5 position.

GRAPHICAL ABSTRACT

Keywords:

• (+)-7-Epi-tarchonanthuslactone
• 1,3-diol/5,6-pyrone
• asymmetric total synthesis
• chelation-controlled Mukaiyama aldol reaction

SUPPORTING INFORMATION

Full experimental details and ¹H, ¹³C NMR, and HRMS spectra for this article can be accessed on the publisher’s website.