A novel synthesis of peptides based on the photochemistry of 5-azido-1, 3, 4-oxadiazoles

PN Confalone, RB Woodward

Index: Confalone, Pat N.; Woodward, Robert B. Journal of the American Chemical Society, 1983 , vol. 105, # 4 p. 902 - 906

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Citation Number: 12

Abstract

Abstract: A novel approach to the synthesis of peptides is described. Various N-protected amino acid hydrazides 17 were converted to the salts 18 by condensation with carbon disulfide in methanolic potassium hydroxide. Thermal cyclization of 18 to the heterocycles 19 was followed by reaction with methyl iodide to yield the sulfides 20. After oxidation of 20 to the corresponding sulfones 21, the title compounds 22 were prepared by treating 21 ...