Total Synthesis of the Cytotoxic Macrocycle (+)-Hitachimycin

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

Research output: Contribution to journalArticlepeer-review

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
DOIs
Publication statusPublished - 1992 Oct 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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