New oxidative tools for the functionalization of the cephalostatin north 1 hemisphere |
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| Authors: | Lee Jong Seok Fuchs Philip L |
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| Institution: | Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA. |
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| Abstract: | Dimethyldioxirane (DMDO) C-H oxidation of ketone 17 to hemiketal 18 (82%), bis-dehydration to vinyl ether 21 (77%), and DMDO again provides C-23 axial alcohol 23 (99%). Routine processing, including a double-stereoselective Sharpless AD reaction (de >98%), gives alcohols 7 and 32. C-23 deoxy substrate 7 undergoes Suarez hypoiodite oxidative cyclization to (natural) beta spiroketal 34, but compound 32, bearing a C-23 silyl ether, generates unnatural spiroketal 33. reaction: see text] |
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