Synthesis of a Regular 24-membered Cyclodepsipeptide by Direct Amide Cyclization

被引：7
作者：
Koettgen, Peter [1 ]
Linden, Anthony [1 ]
Heimgartner, Heinz [1 ]
机构：
[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
来源：
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2009年 / 64卷 / 06期
关键词：
Cyclodepsipeptides; Direct Amide Cyclization; Azirine/Oxazolone Method; Aminoisobutyric Acid; Crystal Structure; ALPHA-AMINO-ACIDS; IN-VITRO SYNTHESIS; CYCLIC DEPSIPEPTIDES; MARINE CYANOBACTERIUM; CONFORMATIONAL-ANALYSIS; CYTOTOXIC CYCLODEPSIPEPTIDES; ENNIATIN; HYDROXY; PEPTIDES; FUNGUS;
D O I：
10.1515/znb-2009-0615
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of a 24-membered cyclic depsipeptide with an alternating sequence of phenyllactic acid and alpha-aminoisobutyric acid (Aib) is described. The linear precursor was prepared via the 'azirine/oxazolone method' using 2,2-dimethyl-3-amino-2H-azirines as building blocks for the alpha,alpha-disubstituted alpha-amino acid Aib. The macrolactonization leading to the cyclodepsipeptide was achieved by the 'direct amide cyclization', i.e., by treatment of a solution of the linear precursor in toluene with HCl gas.
引用
收藏
页码：689 / 698
页数：10
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