Total Synthesis of (+)-Hitachimycin

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The first total synthesis of the macrocyclic antibiotic-antitumor agent (+)-hitachimycin (1) has been achieved via a convergent and efficient route (22 steps, 1.2% overall yield). The key transformation entailed a highly stereoselective, three-component coupling of (-)-5-methoxycyclopentenone (5) with a zincate derived from vinyl iodide 4a and aldehyde (-)-6.

Original languageEnglish
Pages (from-to)1136-1138
Number of pages3
JournalJournal of Organic Chemistry
Volume55
Issue number4
DOIs
Publication statusPublished - 1990 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Smith, A. B., Rano, T. A., Chida, N., & Sulikowski, G. A. (1990). Total Synthesis of (+)-Hitachimycin. Journal of Organic Chemistry, 55(4), 1136-1138. https://doi.org/10.1021/jo00291a005