The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)

Kuniaki Tatsuta, Sonoko Tokishita, Tomohiro Fukuda, Takaaki Kano, Tadaaki Komiya, Seijiro Hosokawa

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

K1115 B1, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B1 by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of 1H NMR spectra and optical rotations made it clear that the absolute structures of K1115 B (the major isomer) and K1115 B (the minor isomer) were (1R, 17S)- and (1R, 17R)-configurations, respectively. The optical rotations of the stereoisomers revealed that alnumycin, reported as the identical structure with K1115 B1, might be another mixture of stereoisomers.

Original languageEnglish
Pages (from-to)983-986
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number9
DOIs
Publication statusPublished - 2011 Mar 2

Keywords

  • Alnumycin
  • BE-41956A
  • K1115 B
  • Michael-Dieckmann type condensation
  • Structural determination
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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