Oxidation of steroid α-diketones by thallium (III) acetate : Crystal and molecular structure of a spiro-cyclopentan-a,s-indaceno derivative obtained from 3,4-diketo steroids |
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| Authors: | AM Maione A Romeo S Cerrini W Fedeli F Mazza |
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| Institution: | Centro di Studio per la Chimica del Farmaco del CNR Istituto di Chimica Farmaceutica dell''Universita, Roma, Italy;Laboratorio di Strutturistica Chimica ''G Giacomello'' CNR C.P.n210,00016 Monterotondo Stazione, Roma, Italy |
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| Abstract: | Treatment of 2,3-diketo-cholestane (1) with thallium triacetate in acetic acid afforded mainly 3α-carbomethoxy-A-nor-5α-cholestan-2-one (2). Under similar conditions, the 3,4-diketo steroids (3 and 4) underwent extensive rearrangement affording spiro-lactones (9 and 10), in low yields. The structural assignment of the spiro-cholestane derivative was supported by crystallographic X-ray analysis. This product was the result of A and B-ring contractions followed by acid-catalysed cyclization of an unsaturated carboxy intermediate. |
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