Synthesis of Chondramide A Analogues with Modified β??Tyrosine and Their Biological Evaluation

…, A Schmauder, CI Ma, LD Sibley, D Sept…

Index: Zhdanko, Alexander; Schmauder, Anke; Ma, Christopher I.; Sibley, L. David; Sept, David; Sasse, Florenz; Maier, Martin E. Chemistry - A European Journal, 2011 , vol. 17, # 47 p. 13349 - 13357

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Citation Number: 15

Abstract

Abstract Starting from cinnamates 9, obtained by Wittig reaction or Heck coupling, the diols 17 were prepared by asymmetric dihydroxylation. This was followed by a regioselective substitution of the 3-OH group with hydrazoic acid under Mitsunobu conditions. Methylation of the 2-OH group and reduction of the azide group led to the β-tyrosine derivatives 8. Condensation with the dipeptide acid 6 furnished the tripeptide part of the chondramides. ...