Formal Total Synthesis of (+)-Gephyrotoxin

An efficient formal total synthesis of (+)-gephyrotoxin is described. The key step of our strategy relies on the diastereoselective reduction of a chiral pyrrolidine β-enamino ester obtained by condensation of (S)-phenylglycinol on a protected 8-hydroxy-3,6-dioxooctanoate.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 73; no. 16; pp. 6466 - 6469
Main Authors Santarem, Marco, Vanucci-Bacqué, Corinne, Lhommet, Gérard
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.08.2008
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Amphibian Venoms - chemical synthesis
Chemical Sciences
Chemistry
Chemistry, Organic
Ethanolamines
Exact sciences and technology
Glycine - analogs & derivatives
Glycine - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Science & Technology
Stereoisomerism
GEPHYROTOXIN
ESTERS
Chemical reduction
Alkaloid
Condensation reaction
Nitrogen heterocycle
Chiral compound
Enaminoester
Protection
Diastereoselectivity
Pyrrolidine derivatives
Total synthesis
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Summary:An efficient formal total synthesis of (+)-gephyrotoxin is described. The key step of our strategy relies on the diastereoselective reduction of a chiral pyrrolidine β-enamino ester obtained by condensation of (S)-phenylglycinol on a protected 8-hydroxy-3,6-dioxooctanoate.
Bibliography:istex:1F9D4010F41A05C6503F10397ED12628877212F4
ark:/67375/TPS-NMVGSZ3Z-D
Experimental procedures and characterization data for compounds 11, 5a−c, 4b, 13, 17, 18, and 2. Copies of 1H and 13C NMR spectra of all compounds. This material is available free of charge via the Internet at http://pubs.acs.org.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo801150e