6-Chloro- and 6-Bromo-Substituted Steroids in the Suzuki-Miyaura Cross-Coupling Reaction. A Convenient Route to Potential Aromatase Inhibitors

Nikolay V. Lukashev; Gennadij V. Latyshev; Pavel A. Donez; George A. Skryabin; Irina P. Beletskaya

doi:10.1055/s-2006-926270

PAPER

6-Chloro- and 6-Bromo-Substituted Steroids in the Suzuki-Miyaura Cross-Coupling Reaction. A Convenient Route to Potential Aromatase Inhibitors

Nikolay V. Lukashev*^a, Gennadij V. Latyshev^a, Pavel A. Donez^a, George A. Skryabin^b, Irina P. Beletskaya^a
^a Chemistry Department, Moscow State Lomonosov University, Vorobievy Gory, 119992, Moscow, Russia
Fax: +7(495)4223297; e-Mail: nvluk@org.chem.msu.su;
^b Ambiotech Inc., 300 E Lombard St. STE 1400, Baltimore, MD 21202, USA

Abstract

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Abstract

Chlorine at an sp²-carbon in steroids has been shown to be reactive in Suzuki-Miyaura cross-coupling reactions with either Ni or Pd catalysts. The coupling of analogous 6-bromo derivatives has also been demonstrated to be applicable to a wider scope of substrates. The Suzuki-Miyaura arylation of 6-bromo-Δ^3,5-steroid enol ethers with subsequent hydrolysis is a useful route to 6-arylated steroids bearing aryl at a saturated carbon.

Key words

cross-coupling - palladium - steroids - Suzuki reaction - nickel

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