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Org Lett. 2013 Apr 5;15(7):1748-51. doi: 10.1021/ol400549q. Epub 2013 Mar 26.

Unexpected Diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin.

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1
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.

Abstract

The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

PMID:
23530662
DOI:
10.1021/ol400549q
[Indexed for MEDLINE]
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