Stereoselective total synthesis and absolute configuration of the natural decanolides (-)-microcarpalide and (+)-lethaloxin. Identity of (+)-lethaloxin and (+)-pinolidoxin.

[reaction: see text] 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.