Intramolecular keto-carbenoid addition to double bonds: stereochemistry of the catalytic reduction of Δ9(11)-gibbenes and related compounds
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 15,p. 548-549
- https://doi.org/10.1039/c39730000548
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.Keywords
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