The Journal of organic chemistry
Synthesis and X-ray Crystal Structure of the Dolabella a uricularia Peptide Dolastatin 18, 1
GR Pettit, F Hogan, DL Herald
Index: Pettit, George R.; Hogan, Fiona; Herald, Delbert L. Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4019 - 4022
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Citation Number: 11
Abstract
A previously synthesized unit of dolastatin 10 (1), dolaphenine (Doe, 3), was converted in four steps to tripeptide 10. Subsequent condensation with carboxylic acid 11 (four steps from Meldrum's acid) provided a practical synthesis of the cancer cell growth inhibitor dolastatin 18 (2, Dhex-(S)-Leu-(R)-N-Me-Phe-Doe). The synthesis of dolastatin 18 (2) confirmed the R stereochemistry of the N-Me-Phe unit as originally assigned and unusual among amino ...