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6β‐Hydroxy‐5β‐methyl‐20‐oxo‐19‐norpregn‐9(10)‐en‐3β‐yl acetate
Authors:R M A Pinto  M Ramos Silva  A Matos Beja  J A R Salvador  J A Paixo
Abstract:In the title compound, C23H34O4, which is an intermediate in the synthesis of pregnane derivatives with a modified skeleton that show potent abortion‐inducing activity, the conformation of ring B is close to half‐chair due to the presence of both the C=C double bond and the axial 5β‐methyl group. Rings A and C have conformations close to chair, while ring D has a twisted conformation around the bridgehead C—C bond. Molecules are hydrogen bonded via the hydroxyl and acetoxy groups into infinite chains. Quantum‐mechanical ab initio Roothan Hartree–Fock calculations show that crystal packing might be responsible for the low values of the angles between rings A and B, and between ring A and rings C and D, as well as for a different steric position of the methyl ketone side chain compared to the geometry of the free molecule.
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