Literature DB >> 17990892

Ammonium chloride promoted three-component synthesis of 5-iminooxazoline and its subsequent transformation to macrocyclodepsipeptide.

Tracey Pirali1, Gian Cesare Tron, Géraldine Masson, Jieping Zhu.   

Abstract

A three-component reaction of an alpha,alpha-disubstituted alpha-isocyanoacetamide, an aldehyde and an amino alcohol afforded the 5-iminooxazoline, which, upon saponification, cyclized under acidic conditions to provide the macrocyclodepsipeptide in good overall yield.

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Year:  2007        PMID： 17990892     DOI： 10.1021/ol7024372

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  2 in total

1.  Isolated α-turn and incipient γ-helix.

Authors:  Fatemeh M Mir; Marco Crisma; Claudio Toniolo; William D Lubell
Journal:  Chem Sci       Date:  2019-06-10       Impact factor: 9.825

2.  Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway.

Authors:  Serge Zaretsky; Jennifer L Hickey; Joanne Tan; Dmitry Pichugin; Megan A St Denis; Spencer Ler; Benjamin K W Chung; Conor C G Scully; Andrei K Yudin
Journal:  Chem Sci       Date:  2015-07-07       Impact factor: 9.825
  2 in total

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