A novel skeletal rearrangement of bicyclo(2.2.2)octenes through bicyclo(3.2.1)octene system: synthesis of (±)-hinesol and (±)-10-epi̲-hinesol

Subba Rao, G. S. R. ; Janaki, Seenivasaga N. (1988) A novel skeletal rearrangement of bicyclo(2.2.2)octenes through bicyclo(3.2.1)octene system: synthesis of (±)-hinesol and (±)-10-epi̲-hinesol Tetrahedron Letters, 29 (25). pp. 3105-3108. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4039(88)85097-4

Abstract

Acid catalysed rearrangement of the endo̲-alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties. An efficient entry into spiro(4.5)decane and eremane system, as exemplified by the total synthesis of (±)-hinesol (2) and its 10-epimer (3) is reported.

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