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: |
|
| 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-dev.library.pitt.edu/id/eprint/16314 |
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