Total syntheses of (±)-β-pinguisene and (±)-pinguisenol

Important ring-skeletons, such as hydroazulene 2, bicyclooctane 4, or hydrindanone 12 can be easily obtained by Amberlyst 15 (A 15) catalyzed cyclizations of allyl- and propargylsilanes. The total syntheses of (±)-β-pinguisene 5 and (±)-pinguisenol 6 have been achieved by propargylsilane-terminated...

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Bibliographic Details
Published in:Tetrahedron 1996-05, Vol.52 (21), p.7475-7485
Main Authors: Schinzer, Dieter, Ringe, Kerstin
Format: Article
Language:English
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Summary:Important ring-skeletons, such as hydroazulene 2, bicyclooctane 4, or hydrindanone 12 can be easily obtained by Amberlyst 15 (A 15) catalyzed cyclizations of allyl- and propargylsilanes. The total syntheses of (±)-β-pinguisene 5 and (±)-pinguisenol 6 have been achieved by propargylsilane-terminated cyclizations of enone 11 as the key step. Compound 12 was transformed in a straight forward way to provide β-pinguisene 5 and pinguisenol 6. Propargylic silane 1 was cyclized with A 15 to give hydrindane 2 which was transformed into β-pinguisene 3 and Pinguisenol 4.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00263-3