Hoye, AT and Wipf, P
(2011)
Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.
Organic Letters, 13 (10).
2634 - 2637.
ISSN 1523-7060
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Abstract
A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented. © 2011 American Chemical Society.
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Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
|
Date: |
20 May 2011 |
Date Type: |
Publication |
Journal or Publication Title: |
Organic Letters |
Volume: |
13 |
Number: |
10 |
Page Range: |
2634 - 2637 |
DOI or Unique Handle: |
10.1021/ol200743u |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
1523-7060 |
MeSH Headings: |
Alkaloids--chemical synthesis; Alkaloids--chemistry; Heterocyclic Compounds, 3-Ring--chemical synthesis; Heterocyclic Compounds, 3-Ring--chemistry; Molecular Structure; Stemonaceae--chemistry; Stereoisomerism |
Other ID: |
NLM NIHMS291055, NLM PMC3099051 |
PubMed Central ID: |
PMC3099051 |
PubMed ID: |
21510628 |
Date Deposited: |
28 May 2013 15:24 |
Last Modified: |
02 Feb 2019 15:57 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/18743 |
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