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Digitale Medien

First Total Synthesis of Enantiomerically Pure(-)-Silphiperfol-6-en-5-onFor a Preliminary communication of this work, see [1a,b][2]. (1988)

Demuth, Martin ; Hinsken, Werner

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 71 (1988), S. 569-576

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Details

ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The angular triquinane (-)-silphiperfol-6-en-5-on ((-)-14) has been synthesized for the first time time in enantiomerically pure form. A highly efficient triplet-sensitized photoreaction, the oxadi-π-methane rearrangement of the complex β,γ-enone(+)-6 to (-)-7, constitutes the key step. The know staring material, (1R, 7aR)-3,6,7,7a-tetrahydro-1-hydroxy-7a-methyl-1H-inden-5(2H)-one ((-)-2), is readily accessible in 〉 97% enantiomeric purity. This new approach should enable access also to other angularly fused triquinanes of the silphinene type and related structures.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19880710309

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