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Org Lett. 2019 Feb 15;21(4):998-1001. doi: 10.1021/acs.orglett.8b04003. Epub 2019 Jan 29.

A General Biomimetic Hetero-Diels-Alder Approach to the Core Skeletons of Xenovulene A and the Sterhirsutins A and B.

Author information

1
Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ) , Leibniz Universität Hannover , Schneiderberg 1 B , 30167 Hannover , Germany.

Abstract

A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.

PMID:
30694066
DOI:
10.1021/acs.orglett.8b04003
[Indexed for MEDLINE]

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