Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol.
[figure: see text] Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.
Gallou
F
F
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
MacMillan
D W
DW
Overman
L E
LE
Paquette
L A
LA
Pennington
L D
LD
Yang
J
J
D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001685:Biological Factors; D001952:Bridged-Ring Compounds; D005663:Furans; C430551:cladiell-11-ene-3,6,7-triol; C412667:sclerophytin A; C412668:sclerophytin B