Download PDF
Synthesis 2013; 45(9): 1261-1269
DOI: 10.1055/s-0032-1316884
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Intramolecular Oxidative Heck Cyclization and Its Application toward a Synthesis of (±)-β-Cuparenone Derivatives Supported by Computational Studies

Devalina Ray
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
,
Yasmin Nasima
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
,
Mal K. Sajal
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
,
Priyanka Ray
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
,
Sharmistha Urinda
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
,
Anakuthil Anoop*
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
,
Jayanta K. Ray*
Department of Chemistry, Indian Institute of Technology, Kharagpur, India   Fax: +91(3222)282252   Email: jkray@chem.iitkgp.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 16 November 2012

Accepted after revision: 11 March 2013

Publication Date:
08 April 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

A novel and efficient intramolecular oxidative cyclization of substituted homoallylic alcohols to form cyclic keto compounds under palladium-catalyzed conditions is described. The reaction has practical applications in the synthesis of sesquiterpenes. The mechanism of cyclization, the key step in the tandem reaction­, was analyzed by using density functional theory calculations.

Key words

palladium - Heck reaction - cyclizations - terpenoids - ketones­ - alkenes - catalysis - oxidations - computational studies

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information