Dolastatins 24. Synthesis of (-)-dolastatin 10. X-Ray molecular structure of N,N-dimethylvalyl-valyl-dolaisoleuine tert-butyl ester

George Pettit, Jayaram K. Srirangam, Sheo Bux Singh, Michael D. Williams, Delbert L. Herald, József Barkóczy, Darko Kantoci, Fiona Hogan

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Total synthesis of the extraordinary antineoplastic constituent, dolastatin 10, from the Indian Ocean mollusc Dolabella auricularia has been summarized. The final synthetic step involved diethyl cyanophosphonate-mediated coupling of Dov-Val-Dil with Dap-Doe. Improved syntheses of these important precursors has led to a very practical synthesis of natural dolastatin 10. Important details of the HPLC and high-field (500 MHz) NMR characterization techniques employed to confirm the purity of dolastatin 10 have been recorded.

Original languageEnglish (US)
Pages (from-to)859-863
Number of pages5
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number8
Publication statusPublished - Apr 21 1996


ASJC Scopus subject areas

  • Organic Chemistry

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