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A novel strategy for the stereoselective total synthesis of c 17 spiro steroids total synthesis of 19 norcanrenone a formal total synthesis of 19 norspironolactone



A novel strategy for the stereoselective total synthesis of c 17 spiro steroids total synthesis of 19 norcanrenone a formal total synthesis of 19 norspironolactone



Journal of the American Chemical Society 110(9): 2931-2938



The intramolecular (4 +2) cycloaddition reactions of olefinic o-quinodimethanes, generated in situ by the thermolysis of olefinic benzocyclobutenes, lead stereoselectively to A-nor B-aromatic C-17 spiro steroids. This is a new and general methodology for the stereoselective synthesis of biologically important C-17 spiro steroids. This method yields the total synthesis of 19-norcanrenone, constituting a formal total synthesis of 19-norspironolactone.

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Accession: 004605868

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DOI: 10.1021/ja00217a040


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