The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene

Srikrishna, Adusumilli and Nagaraju, Gopalasetty (2012) The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene. In: TETRAHEDRON-ASYMMETRY, 23 (2). pp. 170-175.

PDF tet_asy_23-2_170-175_2012.pdf - Published Version Restricted to Registered users only Download (562kB) | Request a copy

Abstract

The enantiospecific total synthesis of silphiperfol-6-ene has been accomplished starting from the readily available monoterpene (R)-limonene, employing a rhodium carbenoid insertion into the CH bond of a tertiary methyl group. A substrate dependent competitive insertion of the rhodium carbenoid in the gamma- and beta-CH bonds to form cyclopentanone and cyclobutanones, respectively, has been described. (C) 2012 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	TETRAHEDRON-ASYMMETRY
Publisher:	Elsevier
Additional Information:	Copyright for this article belongs to Elsevier
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	22 Jun 2012 12:01
Last Modified:	22 Jun 2012 12:03
URI:	http://eprints.iisc.ac.in/id/eprint/44554

Actions (login required)

View Item