Wipf, P and Soth, MJ
(2002)
Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration.
Organic Letters, 4 (10).
1787 - 1790.
ISSN 1523-7060
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Abstract
Matrix presented The convergent synthesis of the fully functionalized C(1)-C(18) segment 24 of the furanocembranes lophotoxin and pukalide was accomplished in 11 steps and 10% overall yield. The key step was a stereoselective conversion of alkynoate 21 to trimethylsilyl 2-alkenylfuran 22.
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Details
| Item Type: |
Article
|
| Status: |
Published |
| Creators/Authors: |
|
| Date: |
16 May 2002 |
| Date Type: |
Publication |
| Journal or Publication Title: |
Organic Letters |
| Volume: |
4 |
| Number: |
10 |
| Page Range: |
1787 - 1790 |
| DOI or Unique Handle: |
10.1021/ol025861m |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Refereed: |
Yes |
| ISSN: |
1523-7060 |
| MeSH Headings: |
Cnidarian Venoms--chemical synthesis; Cnidarian Venoms--chemistry; Cyclization; Epoxy Compounds--chemical synthesis; Epoxy Compounds--chemistry; Furans--chemical synthesis; Furans--chemistry; Magnetic Resonance Spectroscopy; Molecular Conformation; Nicotinic Antagonists--chemical synthesis; Nicotinic Antagonists--chemistry; Receptors, Nicotinic--drug effects; Stereoisomerism; Terpenes--chemical synthesis; Terpenes--chemistry |
| PubMed ID: |
12000299 |
| Date Deposited: |
06 Feb 2014 23:59 |
| Last Modified: |
02 Feb 2019 15:56 |
| URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/20448 |
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