6533b7d2fe1ef96bd125e9d9
RESEARCH PRODUCT
Total Syntheses of Four Stereoisomers of 4α-Hydroxy-1β,7β-peroxy- 10βH-guaia-5-ene
Eva MolinaBegoña GarcíaGonzalo BlayJosé R. Pedrosubject
TandemChemistryStereochemistryLiabum floribundumOrganic ChemistryMoleculeStereoisomerismSelective reductionPhysical and Theoretical ChemistryBiochemistryEne reactionCycloadditiondescription
[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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-06-21 | Organic Letters |