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

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

Research output: Contribution to journalArticle

48 Citations (Scopus)

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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Antibiotics
Aldehydes
Anti-Bacterial Agents
stubomycin
vinyl iodide

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.

Total synthesis of the cytotoxic macrocycle (H-)-hitachimycin. / Smith, Amos B.; Rano, Thomas A.; Chida, Noritaka; Sulikowski, Gary A.; Wood, John L.

In: Journal of the American Chemical Society, Vol. 114, No. 21, 1992, p. 8008-8022.

Research output: Contribution to journalArticle

Smith, AB, Rano, TA, Chida, N, Sulikowski, GA & Wood, JL 1992, 'Total synthesis of the cytotoxic macrocycle (H-)-hitachimycin', Journal of the American Chemical Society, vol. 114, no. 21, pp. 8008-8022.
Smith, Amos B. ; Rano, Thomas A. ; Chida, Noritaka ; Sulikowski, Gary A. ; Wood, John L. / Total synthesis of the cytotoxic macrocycle (H-)-hitachimycin. In: Journal of the American Chemical Society. 1992 ; Vol. 114, No. 21. pp. 8008-8022.
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