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

*この研究の対応する著者

研究成果: Article査読

103 被引用数 (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.

本文言語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
34
DOI
出版ステータスPublished - 1998 9 2
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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