Total syntheses of four stereoisomers of 4alpha-hydroxy-1beta,7beta-peroxy- 10betaH-guaia-5-ene.
[reaction: see text]. The first total syntheses of four stereoisomers of 4alpha-hydroxy-1beta,7beta-peroxy-10betaH-guaia-5-ene are reported starting from the readily available (+)-dihydrocarvone. These compounds have been synthesized from dienes (-)-isoguaiene and (-)-10-epi-isoguaiene by tandem ene hydroperoxylation-[4 + 2] cycloaddition with O(2) followed by selective reduction. The structure of the natural 4alpha-hydroxy-1beta,7beta-peroxy-10betaH-guaia-5-ene isolated from Liabum floribundum has been confirmed.
Blay
Gonzalo
G
Departament de Quimica Orgánica, Facultat de Quìmica, Universitat de València, Spain.
Garcia
Begoña
B
Molina
Eva
E
Pedro
José R
JR
D019659:Asteraceae / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C510336:4alpha-hydroxy-1beta,7beta-peroxy-10betaH-guaia-5-ene; D039821:Monoterpenes