Format

Send to:

Choose Destination
See comment in PubMed Commons below
Org Lett. 2010 Oct 1;12(19):4271-3. doi: 10.1021/ol101646t.

A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group.

Author information

  • 1Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.

Abstract

A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (±)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.

PMID:
20812756
[PubMed - indexed for MEDLINE]
PMCID:
PMC2954672
Free PMC Article
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society Icon for PubMed Central
    Loading ...
    Write to the Help Desk