Total synthesis of eleutherobin and eleuthosides A and B

K. C. Nicolaou, T. Ohshima, S. Hosokawa, F. L. Van Delft, D. Vourloumis, J. Y. Xu, J. Pfefferkorn, S. Kim

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101 Citations (Scopus)

Abstract

The total synthesis of the cytotoxic marine natural products eleutherobin (1) and eleuthosides A (2) and B (3) is described. The strategy involves glycosidation of the (+)-carvone-derived intermediate 7 with the arabinose-derived trichloroacetimidate 9 followed by base-induced ring closure and elaboration to afford the dihydroxy eneynone 19. Selective hydrogenation of 19 led to the generation and intramolecular collapse of dienone 20 furnishing 21 and thence 22 with the required structural framework of the target molecules. Finally, esterification with mixed anhydride 24 followed by deprotection gave eleutherobin (1) which served as a precursor to eleuthosides A (2) and B (3). The α-glycoside anomer of eleutherobin, compound 27, was also synthesized by application of the developed chemistry, demonstrating the flexibility of the sequence in generating designed analogues for biological screening.

Original languageEnglish
Pages (from-to)8674-8680
Number of pages7
JournalJournal of the American Chemical Society
Volume120
Issue number34
DOIs
Publication statusPublished - Sep 2 1998
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Nicolaou, K. C., Ohshima, T., Hosokawa, S., Van Delft, F. L., Vourloumis, D., Xu, J. Y., Pfefferkorn, J., & Kim, S. (1998). Total synthesis of eleutherobin and eleuthosides A and B. Journal of the American Chemical Society, 120(34), 8674-8680. https://doi.org/10.1021/ja9810639