Antineoplastic agents 320: Synthesis of a practical pancratistatin prodrug

George Pettit, S. Freeman, M. J. Simpson, M. A. Thompson, M. R. Boyd, M. D. Williams, G. R. Pettit, D. L. Doubek

Research output: Contribution to journalArticlepeer-review

42 Scopus citations


Owing to its sparingly soluble properties, the potential anticancer drug pancratistatin (1) resisted conventional drug formulation procedures and the synthesis of a water-soluble prodrug became necessary. That important objective for further pre-clinical development was met by devising a route to a disodium phosphate derivative (5). The key step in the synthesis of the phenolic phosphate was phosphorylation of 1,2,3,4-tetraacetoxy-pancratistatin (2) with dibenzyloxy(N,N-diisopropylamido)-phosphine. Subsequent oxidation with m-chloroperbenzoic acid afforded phosphate 4a. Hydrogenolysis of the benzyl esters followed by base-catalysed hydrolysis of the acetate groups led to the water-soluble prodrug 5 in high yield.

Original languageEnglish (US)
Pages (from-to)243-250
Number of pages8
JournalAnti-Cancer Drug Design
Issue number3
StatePublished - 1995

ASJC Scopus subject areas

  • Biochemistry
  • Oncology
  • General Biochemistry, Genetics and Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry


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