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Shichuan Tuo, Xuekui Liu and Peiqiang Huang Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids Chinese Journal of Chemistry 31

Version of Record online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200904

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Completely anti-diastereoselective: This can be achieved by using bromine atom as a traceless directing group in the SmI2-mediated reductive coupling of α,β-unsaturated ester with ketones; or by the one-pot reaction of the organozinc reagent generated from bromomethacrylate with ketone. On the basis of these results, two approaches to the spirolactone moiety with anti-configuration (C-9/C-9a) found in some Stemona alkaloids were disclosed.

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