Total synthesis of the cytotoxic macrocycle (H-)-hitachimycin

Amos B. Smith, Thomas A. Rano, Noritaka Chida, Gary A. Sulikowski, John L. Wood

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Abstract

The first total synthesis of the antitumor antibiotic (+)-hitachimycin (a.k.a. stubomycin) (1) has been achieved in 22 steps and 1.1% overall yield. The cornerstone of the synthetic strategy was a highly stereoselective three-component coupling of (-)-5-methoxycyclopentenone (4) with a zincate derived from vinyl iodide 3a and aldehyde (-)-51.

Original languageEnglish
Pages (from-to)8008-8022
Number of pages15
JournalJournal of the American Chemical Society
Volume114
Issue number21
Publication statusPublished - 1992
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Smith, A. B., Rano, T. A., Chida, N., Sulikowski, G. A., & Wood, J. L. (1992). Total synthesis of the cytotoxic macrocycle (H-)-hitachimycin. Journal of the American Chemical Society, 114(21), 8008-8022.