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RESEARCH PRODUCT
Synthesis of plagiochiline N from santonin.
Begoña GarcíaLuisa LahozGonzalo BlayLuz CardonaJosé R. Pedrosubject
chemistry.chemical_classificationNatural productOzonolysisPlants MedicinalDouble bondDihydropyranStereochemistryAntinematodal AgentsOrganic ChemistryAlkenesRing (chemistry)chemistry.chemical_compoundchemistryMoietySantoninLactoneThiocyanatesSantonindescription
This article reports the transformation of O-acetylisophotosantonin, obtained by photochemical rearrangement of santonin, into plagiochiline N, an ent-2,3-secoaromadendrane isolated from Plagiochila ovalifolia. The synthesis was carried out in a sequence involving as the key steps (a) the substitution of the lactone moiety by a gem-dimethylcyclopropane ring through a synthetic intermediate having a C(6)-C(7) double bond and (b) the ozonolysis of the C(2)-C(3) bond followed by cyclization to the dihydropyran ring characteristic of plagiochiline N. Spectroscopic data of the synthetic product fully coincided with the reported data for the natural product.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-11-10 | The Journal of organic chemistry |