Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of $(\pm)$-Acorone and Isoacorones

Srikrishna, A and Kumar, Praveen P (2000) Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of $(\pm)$-Acorone and Isoacorones. In: Tetrahedron, 56 (41). pp. 8189-8195.

PDF Claisen_rearrangement_based_methodology_for_the_spiroannulation_of_a_cyclopentane_ring._Formal_total_synthesis.pdf Restricted to Registered users only Download (143kB) | Request a copy

Abstract

A Claisen rearrangement based methodology for spiroannulation of a cyclopentane ring to cyclic precursors and its application in the formal total synthesis of acorones 1 is described. Thus, Claisen rearrangement of 2-cycloalkylideneethanols 12 with 2-methoxypropene and a catalytic amount of mercuric acetate generates 4,4-substituted hex-5-en-2-ones 13. Ozonolytic cleavage of the terminal olefin in the enones 13 and intramolecular aldol condensation of the resulting keto-aldehydes 14 furnishes the spiroannulated compounds 15.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier
Additional Information:	Copyright of this article belongs to Elsevier.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	09 Oct 2007
Last Modified:	19 Sep 2010 04:40
URI:	http://eprints.iisc.ac.in/id/eprint/12168

Actions (login required)

View Item