Journal
TETRAHEDRON
Volume 67, Issue 20, Pages 3668-3676Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.080
Keywords
Aza steroids; Pyridine; Intramolecular Diels-Alder reaction; Wacker-type oxidation
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An efficient synthesis of 11-selena and 11-tellura steroids bearing a pyridine as an A ring was achieved via an intramolecular Diels-Alder cycloaddition of o-quinodimethanes, which were generated from a 3-azabicyclo[4.2.0]octa-1,3,5-trien-7-one ketal. The major isomer matches the trans-anti-trans ring configuration of natural products. Finally, the vinyl groups of the synthesized 11-hetero steroids have been oxidized by the Wacker process in good yields. The characteristic H-1 and C-13 NMR spectroscopic features of the synthesized compounds are reported. (C) 2011 Elsevier Ltd. All rights reserved.
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