PMID: 11312944Apr 21, 2001Paper

Mimicry of peptide backbone geometry and heteroatomic side-chain functionality: synthesis of enantiopure indolizidin-2-one amino acids possessing alcohol, acid, and azide functional groups

The Journal of Organic Chemistry
Felix Polyak, William D Lubell

Abstract

Indolizidinone amino acids possessing various heteroatomic side chains at their 5- and 7-positions have been synthesized through modification of hydroxymethyl indolizidinone amino acids 5 and 6. Displacements of the methanesulfonates from alcohols 5 and 6 with sodium azide, as well as oxidation of alcohol 5, have been used to furnish orthogonally protected indolizidin-2-one diamino carboxylates 7 and 8, and indolizidin-2-one amino dicarboxylate 9. Both 5- and 7-hydroxymethylindolizidinone amino acids 5 and 6 were obtained from sequences commencing with the Claisen condensation of alpha-tert-butyl gamma-methyl l-N-(PhF)-L-glutamate to furnish di-tert-butyl 4-carbomethoxy-5-oxo-2,8-di-[N-(PhF)amino]azelate 10 (PhF = 9-(9-phenylfluorenyl)). Subsequent hydride reduction of 10 to an isomeric mixture of diols 12, selective protection of the primary alcohol as tert-butyldimethylsilyl ether 14 and oxidation of the secondary alcohol gave di-tert-butyl 4-tert-butyldimethylsilyloxymethyl-5-oxo-2,8-di-[N-(PhF)amino]azelate 15 as a separable diastereomeric mixture. Linear ketone 15 and alcohol 14 were then converted to the indolizidinone heterocycles by routes featuring reductive aminations, methanesulfonate displacements, and lactam cycliz...Continue Reading

Citations

Aug 19, 2007·Amino Acids·A TrabocchiA Guarna
Feb 6, 2010·Journal of the American Chemical Society·Hai-Chao Xu, Kevin D Moeller
Jul 27, 2005·Angewandte Chemie·Reinhard W Hoffmann
Jun 6, 2014·Organic & Biomolecular Chemistry·Arkady Khashper, William D Lubell
May 22, 2008·Organic Letters·David KesselringKevin D Moeller
Sep 11, 2009·The Journal of Organic Chemistry·Tina MittagTroels Skrydstrup
Jul 18, 2002·Journal of the American Chemical Society·Peter Tremmel, Armin Geyer
Oct 27, 2004·Angewandte Chemie·Peter Tremmel, Armin Geyer
Jan 28, 2005·Angewandte Chemie·K C NicolaouBrian S Safina
Jan 27, 2007·The Journal of Organic Chemistry·Mallem H V Ramana RaoWilliam D Lubell
Aug 30, 2003·The Journal of Organic Chemistry·Evelyne Dietrich, William D Lubell
Mar 1, 2003·The Journal of Organic Chemistry·Gianluigi LuppiClaudia Tomasini
May 13, 2004·Chemical Reviews·Alessandro Dondoni, Alberto Marra
Jun 2, 2007·The Journal of Organic Chemistry·Erik ChorellFredrik Almqvist
May 7, 2005·The Journal of Organic Chemistry·Leonardo ManzoniCarlo Scolastico

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