Cg. Shin et al., SYNTHESES OF O-3-CARBOXY-3-HYDROXYPROPYL]-THIAZOLE-4-CARBOXYLIC ACID AND THE TRIPEPTIDE SKELETON OF NOSIHEPTIDE CONTAINING THE ACID, Bulletin of the Chemical Society of Japan, 68(11), 1995, pp. 3151-3160
The stereoselective synthesis of an amino acid component called Fragme
nt D, N,O-diprotected 2-[(1S, no-3-carboxy-3-hydroxypropyl]thiazole-4-
carboxylic acid of a macrobicyclic peptide antibiotic nosiheptide, was
achieved by two routes. The dipeptide, Fragment B-C, 2-[(Z)-1-(N, O-i
sopropylidene-L-threonylamino)-1-propenyl] thiazole-4-carboxylic acid
was also synthesized by the thiazole ring formation from (Z)-2-(N, O-d
iprotected L-threonylamino)-2-butenethioamide with ethyl bromopyruvate
. The coupling of two components by using a condensing agent gave the
expected tripeptide 2, which is an important partial skeleton of the n
osiheptide.