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.

Preview

PDF 222.pdf Download (685kB)

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
Publication:	Phytochemistry
Publisher:	Elsevier
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.ac.in/id/eprint/14304

Actions (login required)

View Item