PMID: 11312945Apr 21, 2001Paper

Synthesis of enantiopure 7-[3-azidopyl]indolizidin-2-one amino acid. A constrained mimic of the peptide backbone geometry and heteroatomic side-chain functionality of the ala-lys dipeptide

The Journal of Organic Chemistry
Z Feng, William D Lubell

Abstract

Enantiopure N-(BOC)amino-7-[3-azidopropyl]indolizidin-2-one acid 1 has been synthesized by displacement of the methanesulfonate of its 7-hydroxypropyl counterpart 11 with sodium azide and subsequent ester hydrolysis. N-(BOC)Amino-7-[3-hydroxypropyl]indolizidin-2-one ester 11 was obtained from a sequence commencing with the alkylation of (2S,8S)-di-tert-butyl 5-oxo-2,8-di-[N-(PhF)amino]azelate 5 (PhF = 9-(9-phenylfluorenyl)). Stereoselective allylation of 5, regioselective olefin hydroboration, selective primary alcohol protection as a silyl ether, and oxidation of the secondary alcohol gave (2S,4R,8S)-di-tert-butyl 4-[3-tert-butyldimethylsiloxypropyl]-5-oxo-2,8-di-[N-(PhF)amino]azelate 9 as a pure diastereomer in 33% overall yield. Linear ketone 9 was then converted into the indolizidinone heterocycle by a route featuring reductive amination, lactam cyclization, and isolation by way of a silyl ether which provided the (6S,7R)-isomer of 11.

Citations

Feb 6, 2010·Journal of the American Chemical Society·Hai-Chao Xu, Kevin D Moeller
Feb 12, 2005·The Journal of Peptide Research : Official Journal of the American Peptide Society·Z Sajjadi, W D Lubell
May 22, 2008·Organic Letters·David KesselringKevin D Moeller
Jan 27, 2007·The Journal of Organic Chemistry·Mallem H V Ramana RaoWilliam D Lubell
May 13, 2004·Chemical Reviews·Alessandro Dondoni, Alberto Marra
May 7, 2005·The Journal of Organic Chemistry·Leonardo ManzoniCarlo Scolastico

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