Issue 15, 1973

Intramolecular keto-carbenoid addition to double bonds: stereochemistry of the catalytic reduction of Δ9(11)-gibbenes and related compounds

Abstract

Decomposition of some γδ-unsaturated α-diazomethyl ketones using an ‘activated CuO catalyst’ under irradiation with a tangsten lamp results in a significant increase in the yields of the corresponding intramolecular keto-carbenoid addition products; the substituents effect in controlling the stereoselectivity in the catalytic hydrogenation of a few pentacyclic ketones and Δ9(11)-gibbene derivatives have been evaluated, leading to stereocontrolled syntheses of some C-9 epimeric gibbane synthons and a degradation product of gibberellin A13.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1973, 548-549

Intramolecular keto-carbenoid addition to double bonds: stereochemistry of the catalytic reduction of Δ9(11)-gibbenes and related compounds

U. R. Ghatak, P. C. Charkraborti, B. C. Ranu and B. Sanyal (<em xmlns="http://www.rsc.org/schema/rscart38">née</em> Moitra), J. Chem. Soc., Chem. Commun., 1973, 548 DOI: 10.1039/C39730000548

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