A stereoselective aldol approach for the total syntheses of two 6-Alkylated 2H-pyran-2-ones

Abstract

A simple and highly efficient stereoselective total synthesis of the 6-alkylated pyranones (6R)-6-[(1E,4R,6R)-4,6-dihydroxy-10-phenyldec-1-en-1-yl]- 5,6-dihydro-2H-pyran-2-one (1) and (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6- phenylhexyl]-2H-pyran-2-one (2) was developed using Crimmins' aldol reaction, SmI2 reduction, Grubbs-II-catalyzed olefin cross-metathesis, and Still's modified Horner-Wadsworth-Emmons reaction. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.