Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (19) , 6587-6590
- https://doi.org/10.1021/jo960361q
Abstract
Oxidation of 5-unsaturated 3β-hydroxy steroids 1 to the corresponding 4-en-3-one derivatives 2 can be performed efficiently by acetone at reflux in the presence of a catalytic system consisting of either (PPh3)3RuCl2 (3) and K2CO3 or [(C4Ph4COHOCC4Ph4)(μ-H)][(CO)4Ru2] (4). The reaction proceeds via a ruthenium-catalyzed dehydrogenation of 1 and subsequent hydrogen transfer to acetone with concomitant double bond migration.Keywords
This publication has 18 references indexed in Scilit:
- Ruthenium-Catalyzed Oxidation of Nonactivated Alcohols by MnO2The Journal of Organic Chemistry, 1994
- Ruthenium-catalysed oxidation of alcohols by acetoneJournal of the Chemical Society, Chemical Communications, 1992
- Selective aromatization of the A ring of steroids through demethylation by an electrophilic ruthenium fragmentJournal of the Chemical Society, Chemical Communications, 1991
- Complete assignments of the 1H and 13C NMR spectra of testosterone and 17α‐methyltestosterone and the 1H parameters obtained from 600 MHz spectraMagnetic Resonance in Chemistry, 1990
- Natural abundance 17O NMR spectra of coumarins, furocoumarins and related compoundsMagnetic Resonance in Chemistry, 1987
- Aufbau der Corticoid‐Seitenkette aus 17α‐(Halogenethinyl)‐17β‐(nitrooxy)androstenenEuropean Journal of Organic Chemistry, 1987
- Synthesis of 6-deoxohomodolichosterone, a new plant-growth-promoting steroidJournal of the Chemical Society, Perkin Transactions 1, 1986
- An improved route to 19-hydroxypregn-4-ene-3,20-dione and synthesis of its [19-2H2] analogueJournal of the Chemical Society, Perkin Transactions 1, 1983
- Biomimetic polyene cyclizations. Participation of the methylacetylenic terminator and nitroalkanes. A synthesis of testosteroneJournal of the American Chemical Society, 1980
- Naturally Occurring Aromatic SteroidsPublished by Wiley ,1973