Synthesis of the C(1)−C(18) Segment of Lophotoxin and Pukalide. Control of 2-Alkenylfuran (E/Z)-Configuration

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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Bibliographic Details
Published inOrganic letters Vol. 4; no. 10; pp. 1787 - 1790
Main Authors Wipf, Peter, Soth, Michael J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.05.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
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
Physical Sciences
Receptors, Nicotinic - drug effects
Science & Technology
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
REARRANGEMENT
ORGANIC-SYNTHESIS
DIELS-ALDER REACTIONS
FURANOCEMBRANOLIDES
ASYMMETRIC CYCLOADDITION REACTIONS
BETA-KETO-ESTERS
DERIVATIVES
ACYLSILANES
MACROCYCLIZATION
VINYLSILANES
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025861m