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.
García-Fortanet
Jorge
J
Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12071 Castellón, Spain.
Murga
Juan
J
Falomir
Eva
E
Carda
Miguel
M
Marco
J Alberto
JA
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000473:Alkanes; D000475:Alkenes; D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; C442266:microcarpalide; C410769:pinolidoxin