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

研究成果: Article

101 引用 (Scopus)

抄録

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.

元の言語English
ページ(範囲)8674-8680
ページ数7
ジャーナルJournal of the American Chemical Society
120
発行部数34
DOI
出版物ステータスPublished - 1998 9 2
外部発表Yes

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Glycosides
Esterification
Hydrogenation
Screening
Molecules
Arabinose
Anhydrides
Biological Products
eleutherobin

ASJC Scopus subject areas

  • Chemistry(all)

これを引用

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.

:: Journal of the American Chemical Society, 巻 120, 番号 34, 02.09.1998, p. 8674-8680.

研究成果: Article

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, 巻. 120, 番号 34, pp. 8674-8680. https://doi.org/10.1021/ja9810639
Nicolaou KC, Ohshima T, Hosokawa S, Van Delft FL, Vourloumis D, Xu JY その他. Total synthesis of eleutherobin and eleuthosides A and B. Journal of the American Chemical Society. 1998 9 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. :: Journal of the American Chemical Society. 1998 ; 巻 120, 番号 34. pp. 8674-8680.
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