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Regio-and Stereospecific Construction of Vicinal Quaternary Carbons: Total Synthesis of (±)-Albene

Srikrishna, Adusumilli and Nagaraju, Sankuratri (1995) Regio-and Stereospecific Construction of Vicinal Quaternary Carbons: Total Synthesis of (±)-Albene. In: Phytochemistry, 40 (6). pp. 1699-1704.

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Abstract

A regiospecific and stereoselective total synthesis of the trisnorsesquiternene (±)-albene, via a prochiral precursor is described. The ortho ester Claisen rearrangement of the allyl alcohol, obtained in two regiospecific reactions from a Diels-Alder adduct, followed by hydrolysis of the resultant ester furnished an ene acid in a highly stereoselective manner. Anhydrous copper sulphate catalysed intramolecular cyclopropanation reaction of the diazo ketone derived from the ene acid, generated a cyclopropyl ketone. The regiospecific reductive cleavage of this cyclopropyl ketone resulted in a prochiral ketone. Finally, Shapiro reaction on the tosylhydrazone, derived from the latter ketone, furnished (±)-albene.

Item Type: Journal Article
Additional Information: Copyright belongs to Elsevier.
Keywords: Albene;quaternary carbons;Claisen rearrangement;diazo ketone;cyclopropanation;reductive cycopropane cleavage;Shapiro reaction.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 13 Jun 2008
Last Modified: 19 Sep 2010 04:45
URI: http://eprints.iisc.ernet.in/id/eprint/14304

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