Enantioselective approach to the asymmetric synthesis of(6R)-hydroxymethyl-5,6-dihydro-2H-pyran-2-one. A formal synthesis of(R)-argentilactone and total synthesis of (R)-goniothalamin

Abstract

The asymmetric synthesis of the (6R)-hydroxymethyl-5,6-dihydro-2H-pyran-2- one, a key intermediate in the formal synthesis of (R)-argentilactone, and the total synthesis of (R)-goniothalamin are described. Our aproach involved the Lemieux-Johnson oxidative cleavage, enantioselective Keck allylation, ring-closing metathesis and Wittig olefination.