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

54 Citations (Scopus)


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
Issue number21
Publication statusPublished - 1992 Oct 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


Dive into the research topics of 'Total Synthesis of the Cytotoxic Macrocycle (+)-Hitachimycin'. Together they form a unique fingerprint.

Cite this