Stereoselective Total Synthesis and Absolute Configuration of the Natural Decanolides (−)-Microcarpalide and (+)-Lethaloxin. Identity of (+)-Lethaloxin and (+)-Pinolidoxin

Convergent, stereoselective syntheses of the pharmacologically active, naturally occurring lactones
(−)-microcarpalide and (+)-lethaloxin have been achieved from the commercially available, chiral
reagents (R)-glycidol, (S,S)-tartaric acid, and d-ribose as the starting materials. These syntheses
have further served to establish the hitherto unknown absolute configuration of (+)-lethaloxin and
to show its identity with (+)-pinolidoxin.