Total syntheses of four stereoisomers of 4alpha-hydroxy-1beta,7beta-peroxy- 10betaH-guaia-5-ene |
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Authors: | Blay Gonzalo Garcia Begoña Molina Eva Pedro José R |
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Institution: | Departament de Quimica Orgánica, Facultat de Quìmica, Universitat de València, Spain. |
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Abstract: | 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. |
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