Stereoselective synthesis of the gamma-lactam hydrolysate of the thiopeptide cyclothiazomycin

Organic Letters
Mark C Bagley, Xin Xiong

Abstract

[reaction: see text] Bohlmann-Rahtz pyridine synthesis of a chiral nonracemic enamine and thiazolylpropynone gives a terminal-protected pyridine-containing gamma-amino acid in high optical purity in a sequential one-pot multicomponent reaction that proceeds with total control of regiochemistry and with minimal racemization. Further elaboration has established the synthesis of the gamma-lactam acidic hydrolysate of the macrocyclic thiopeptide antibiotic cyclothiazomycin, a selective renin inhibitor, in only four steps and 30% overall yield and has confirmed its structure.

References

Nov 7, 2003·Organic Letters·Mark C BagleyJustin Bower
Jan 23, 2004·Chemical Communications : Chem Comm·Mark C BagleyJustin Bower

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Citations

Jun 3, 2006·Natural Product Reports·Zhong Jin
Jan 22, 2014·Marine Drugs·Xavier Just-BaringoMercedes Álvarez
Jul 19, 2011·Organic Letters·Yan ZouAlexander Deiters
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mark C Bagley, Christian Glover
Sep 15, 2007·Angewandte Chemie·Rachael A Hughes, Christopher J Moody
Feb 14, 2008·Chemistry : a European Journal·Oscar DelgadoThorsten Bach
Aug 25, 2010·Organic & Biomolecular Chemistry·Anupam BandyopadhyayHosahudya N Gopi
Oct 21, 2010·Chemistry : a European Journal·Carolin Ammer, Thorsten Bach
Feb 16, 2016·Beilstein Journal of Organic Chemistry·Tarn C Johnson, Stephen P Marsden
Nov 10, 2013·Beilstein Journal of Organic Chemistry·Mark C BagleyChristopher Mason
Feb 11, 2005·Chemical Reviews·Mark C BagleyXin Xiong
Feb 12, 2005·The Journal of Organic Chemistry·Mark C BagleyJustin Bower
Aug 13, 2005·The Journal of Organic Chemistry·Mark C BagleyRobin Wood

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