ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A New 3-Amino-2H-azirine as an Aib-Pro Synthon: Synthesis of the C-Terminal Nonapeptide of Trichovirin I 1BThe synthesis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (3), a novel 3-amino-2H-azirine, is described (Scheme 2). It is shown that the reaction of COCl2 with thioamide 5 is remarkably faster than with the corresponding amide 4, and the yield of 3 is much better in the synthesis starting with 5. The 3-amino-2H-azirine 3 has been used as a building block of the dipeptide moieties Aib-Pro in the synthesis of nonapeptide 17 (Schemes 4 and 5), the C-terminal 6-14 segment of the peptaibole trichovirin I 1B. The structure of 17 was established by single-crystal X-ray crystallography (Figs.1 and 2).
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19960790220
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