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Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration

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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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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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Soth, MJ
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


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