The dolastatins 16. Synthesis of dolaphenine

George Pettit, Fiona Hogan, Douglas D. Burkett, Sheo B. Singh, Darko Kantoci, Jayaram Srirangam, Michael D. Williams

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

Synthesis of dolaphenine (2), the thiazole-containing unit of the strongly antineoplastic peptide dolastatin 10 (1), has been summarized. While conversion (4→7 or 4→11) of phenylalanine to thiazolidines (7) or thiazolines (11) was routinely uneventful, a dependable procedure for dehydrogenation of these intermediates to dolaphenine (2, Doe) proved elusive. While several types of specially prepared manganese dioxide were found most effective for the dehydrogenation, yields of dolaphenine varied from almost nil to over 70%. Some of these reactions resulted in partial to complete racemization of the phenylalanine derived chiral carbon.

Original languageEnglish (US)
Pages (from-to)81-100
Number of pages20
JournalHeterocycles
Volume39
Issue number1
DOIs
StatePublished - Dec 31 1994

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The dolastatins 16. Synthesis of dolaphenine'. Together they form a unique fingerprint.

  • Cite this

    Pettit, G., Hogan, F., Burkett, D. D., Singh, S. B., Kantoci, D., Srirangam, J., & Williams, M. D. (1994). The dolastatins 16. Synthesis of dolaphenine. Heterocycles, 39(1), 81-100. https://doi.org/10.3987/com-93-s(b)2