Tetrahedron letters

Rubrenolide, total synthesis and assignment of its absolute configuration.

T Saito, L Thijs, GJ Ettema, B Zwanenburg

Index: Saito, Takao; Thijs, Lambertus; Ettema, Gert-Jan; Zwanenburg, Binne Tetrahedron Letters, 1993 , vol. 34, # 22 p. 3589 - 3592

Full Text: HTML

Citation Number: 12

Abstract

Abstract The total synthesis of rubrenolide 1, a naturally occuring γ-lactone, is described. The γ-lactone was prepared by using the photo-induced rearrangement of an epoxy diazomethyl ketone as the key step. The diol side chain was introduced by a condensation with isopropylidene glyceraldehyde. During the synthesis it was concluded that the stereochemistry of the secondary alcohol was orinally incorrectly assigned. Rubrenolide ...