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A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane

Zhang, H and Curran, DP (2011) A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane. Journal of the American Chemical Society, 133 (27). 10376 - 10378. ISSN 0002-7863

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Abstract

The first stereoselective synthesis of epimeloscine has been accomplished in 13 total steps with a longest linear sequence of 10 steps. The core of the synthesis takes only five steps, the key ones being acylation, stereoselective tandem radical cyclization of a divinylcyclopropane to make two rings, and group-selective ring-closing metathesis of the resulting divinylcyclopentane to make the last ring. © 2011 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, H
Curran, DPcurran@pitt.eduCURRAN
Date: 13 July 2011
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 133
Number: 27
Page Range: 10376 - 10378
DOI or Unique Handle: 10.1021/ja2042854
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Acylation; Cyclization; Cyclopropanes--chemistry; Polycyclic Compounds--chemical synthesis; Quinolines--chemical synthesis; Stereoisomerism; Vinyl Compounds--chemistry
Other ID: NLM NIHMS304591, NLM PMC3131464
PubMed Central ID: PMC3131464
PubMed ID: 21663316
Date Deposited: 16 Nov 2012 16:05
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/16314

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