Synthesis of griseolic acid analogues: regioselective a-facial [1,2]-migration in the rhodium acetate catalyzed reaction of D-glucose derived α-diazo-β-keto ester

Karche, Navnath P. ; Jachak, Santosh M. ; Dhavale, Dilip D. (2003) Synthesis of griseolic acid analogues: regioselective a-facial [1,2]-migration in the rhodium acetate catalyzed reaction of D-glucose derived α-diazo-β-keto ester Journal of Organic Chemistry, 68 (11). pp. 4531-4534. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo026858j

Related URL: http://dx.doi.org/10.1021/jo026858j

Abstract

This paper describes an efficient route for the synthesis of known and novel griseolic acid analogues 1d and 1e, respectively. The key intermediate dioxabicyclo derivative 6, with the required stereochemical orientation at C6, was obtained by rhodium acetate catalyzed reaction of D-glucose derived α-diazo-β-keto ester 5 in a novel high-yielding methodology.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:75348
Deposited On:22 Dec 2011 13:10
Last Modified:22 Dec 2011 13:10

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