Stereoselective Total Synthesis of Natural Decanolides Bellidisin C and Pinolidoxin

Abstract

A divergent total synthesis of bioactive, naturally occurring decanolides, pinolidoxin and bellidisin C, was accomplished by taking advantage of chiral templates L-ribose and L-malic acid. In particular, bellidisin C, which is the first total synthesis so far, was achieved through a cascade reaction of reductive elimination and nucleophilic addition in a one-pot process and a sodium–alkoxide-promoted intramolecular lactonization as the key steps.

Keywords

• decanolide
• bellidisin C
• pinolidoxin
• total synthesis