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Stereoselective syntheses of unnatural steroidal C(20R) aldehydes by ionic hydrogenation of C-20 tertiary alcohols |
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| Authors: | Bapurao B. Shingate Braja G. Hazra Vandana S. Pore Rajesh G. Gonnade Mohan M. Bhadbhade |
| Affiliation: | aOrganic Chemistry Synthesis Division, National Chemical Laboratory, Pune 411 008, India bCentre for Materials Characterization, National Chemical Laboratory, Pune 411 008, India |
| Abstract: | Syntheses of three unnatural steroidal C(20R) aldehydes have been realised from 16-dehydropregnenolone acetate. The salient feature of the synthesis is the ionic hydrogenation of C-20 tertiary alcohols leading to the formation of the C(20R) unnatural isomer with complete stereoselectivity. Oxidative hydrolysis of the dithiane moiety furnished the C(20R) aldehydes. |
| Keywords: | Stereoselective synthesis Ionic hydrogenation 1,3-Dithiane Unnatural C-20 aldehydes Oxidative hydrolysis |
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