Total synthesis of eleutherobin and eleuthosides A and B

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

Research output: Contribution to journalArticle

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 - 1998 Sep 2
Externally publishedYes

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Glycosides
Esterification
Hydrogenation
Screening
Molecules
Arabinose
Anhydrides
Biological Products
eleutherobin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

Total synthesis of eleutherobin and eleuthosides A and B. / Nicolaou, K. C.; Ohshima, T.; Hosokawa, Seijiro; Van Delft, F. L.; Vourloumis, D.; Xu, J. Y.; Pfefferkorn, J.; Kim, S.

In: Journal of the American Chemical Society, Vol. 120, No. 34, 02.09.1998, p. 8674-8680.

Research output: Contribution to journalArticle

Nicolaou, KC, Ohshima, T, Hosokawa, S, Van Delft, FL, Vourloumis, D, Xu, JY, Pfefferkorn, J & Kim, S 1998, 'Total synthesis of eleutherobin and eleuthosides A and B', Journal of the American Chemical Society, vol. 120, no. 34, pp. 8674-8680. https://doi.org/10.1021/ja9810639
Nicolaou KC, Ohshima T, Hosokawa S, Van Delft FL, Vourloumis D, Xu JY et al. Total synthesis of eleutherobin and eleuthosides A and B. Journal of the American Chemical Society. 1998 Sep 2;120(34):8674-8680. https://doi.org/10.1021/ja9810639
Nicolaou, K. C. ; Ohshima, T. ; Hosokawa, Seijiro ; Van Delft, F. L. ; Vourloumis, D. ; Xu, J. Y. ; Pfefferkorn, J. ; Kim, S. / Total synthesis of eleutherobin and eleuthosides A and B. In: Journal of the American Chemical Society. 1998 ; Vol. 120, No. 34. pp. 8674-8680.
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