eprintid: 20448
rev_number: 16
userid: 1419
dir: disk0/00/02/04/48
datestamp: 2014-02-06 23:59:20
lastmod: 2019-02-02 15:56:54
status_changed: 2014-02-06 23:59:20
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Wipf, P
creators_name: Soth, MJ
creators_email: pwipf@pitt.edu
creators_email: 
creators_id: PWIPF
creators_id: 
title: Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2002-05-16
date_type: published
publication: Organic Letters
volume: 4
number: 10
pagerange: 1787 - 1790
refereed: TRUE
issn: 1523-7060
id_number: 10.1021/ol025861m
pmid: 12000299
mesh_headings: Cnidarian Venoms--chemical synthesis
mesh_headings: Cnidarian Venoms--chemistry
mesh_headings: Cyclization
mesh_headings: Epoxy Compounds--chemical synthesis
mesh_headings: Epoxy Compounds--chemistry
mesh_headings: Furans--chemical synthesis
mesh_headings: Furans--chemistry
mesh_headings: Magnetic Resonance Spectroscopy
mesh_headings: Molecular Conformation
mesh_headings: Nicotinic Antagonists--chemical synthesis
mesh_headings: Nicotinic Antagonists--chemistry
mesh_headings: Receptors, Nicotinic--drug effects
mesh_headings: Stereoisomerism
mesh_headings: Terpenes--chemical synthesis
mesh_headings: Terpenes--chemistry
chemical_names: Cnidarian Venoms
chemical_names: Epoxy Compounds
chemical_names: Furans
chemical_names: Nicotinic Antagonists
chemical_names: Receptors, Nicotinic
chemical_names: Terpenes
chemical_names: pukalide
chemical_names: lophotoxin
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/20448/1/licence.txt