Configurations of alcohols obtained from dihydro- O -acetylisophoto-α-santonic lactone

Marrero, Benito García

doi:10.1016/s0040-4020(00)01133-9

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Vetisperane and Spiroaxane1

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2001

2002

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Cited by 2 publications

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“…Treatment of compound 6b with NaBH 4 in MeOH gave the major alcohol 7 in 93% yield. The stereochemistry of the resulting alcohol was proposed on the assumption of a preferred attack of the hydride from the less hindered α-side of the molecule 1 …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Plagiochiline N from Santonin

et al. 2001

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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.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Plagiochiline N from Santonin

et al. 2001

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“…362 The structure of cichopumilide must be corrected, because it has been proved to be identical with magnolialide, a eudesmanolide. 308 The configurations of the alcohols obtained from dihydro-O-acetylisophoto-α-santonic lactone have been revised, 363 whilst the absolute configuration of matricin has been confirmed. 364 The microbiological transformation of dehydrocostuslactone with different fungi has been investigated.…”

Section: Vetisperane and Spiroaxanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2002

Nat. Prod. Rep.

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Configurations of alcohols obtained from dihydro- O -acetylisophoto-α-santonic lactone

Cited by 2 publications

References 14 publications

Synthesis of Plagiochiline N from Santonin

Synthesis of Plagiochiline N from Santonin

Natural sesquiterpenoids

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