The cephalostatins. 23. Conversion of hecogenin to a steroidal 1,6-dioxaspiro[5.5]nonane analogue for cephalostatin 11

George Pettit, Bryan R. Moser, Delbert L. Herald, John C. Knight, Jean Chapuis, Xing Zheng

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Cephalostatin 1 (1) has proved to be a remarkably potent cancer cell growth inhibitor. Since this steroidal alkaloid constituent of the marine worm Cephalodiscus gilchristi possesses a complex structure, providing preclinical supplies by total synthesis continues to be challenging. Therefore, syntheses of less complex structural modifications of this important pyrazine have also received substantial attention. Herein are summarized the synthesis of [5.5]spiroketal 5, a simplified right-side steroidal unit of 1, in seven steps from hecogenin acetate (11) with an overall yield of 4.6%. Consistent with other SAR studies, such reduction in structural complexity compared to 1 led to loss of cancer cell growth inhibitory activity against the P388 lymphocytic leukemia cell line.

Original languageEnglish (US)
Pages (from-to)1067-1072
Number of pages6
JournalJournal of Natural Products
Volume78
Issue number5
DOIs
StatePublished - May 22 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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