Total Synthesis of Bistratamide D

The total synthesis of the macrocyclic hexapeptide bistratamide D is reported. The synthetic strategy involved assembly of enantiomerically pure oxazole, thiazole, and oxazoline segments derived from amino acids. Macrocyclization of the hexapeptidic aminooxazoline-oxazole-thiazole carboxylic acid fr...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 3; pp. 826 - 831
Main Authors Downing, Susan V, Aguilar, Enrique, Meyers, A. I
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
PATELLAMIDES-B
REAGENTS
NUDIBRANCH EGGMASSES
SPONGE THEONELLA SP
AMINO-ACIDS
TOXIC CYCLIC PEPTIDE
TUNICATE
BIOACTIVE MARINE METABOLITES
MACROLIDES
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Summary:The total synthesis of the macrocyclic hexapeptide bistratamide D is reported. The synthetic strategy involved assembly of enantiomerically pure oxazole, thiazole, and oxazoline segments derived from amino acids. Macrocyclization of the hexapeptidic aminooxazoline-oxazole-thiazole carboxylic acid fragment was accomplished by activation with O-(7-azabenzotriazol-1-yl)-N,N,N‘,N‘-tetramethyluronium hexafluorophosphate (HATU).
Bibliography:Dedicated to Professor Teruaki Mukaiyama on the occasion of his 75th birthday.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo981664i