Redox refunctionalization of steroid spiroketals. Structure correction of ritterazine M |
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Authors: | Lee Seongmin LaCour Thomas G Lantrip Douglas Fuchs Philip L |
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Institution: | Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA. |
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Abstract: | The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal-alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the spiroketal and Sharpless asymmetric dihydroxylation of an isopentyl, methyl 1,1-disubstituted olefin, followed by Suarez iodineIII] oxidative spirocyclization of monoprotected 1 degree,3 degree 1,2 diols. |
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