Stereochemistry of theonezolides A-C

Kohei Nozawa, Masashi Tsuda, Naonobu Tanaka, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Jun'Ichi Kobayashi

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Theonezolides A-C (1-3) are cytotoxic 37-membered macrolides with a long side chain isolated from an Okinawan marine sponge Theonella sp. The relative stereochemistry of 1-3 was investigated by combination of NMR analysis including application of a JBCA method, a Universal NMR database, and a 13C-acetonide method. Furthermore, the absolute configurations at 14 chiral centers in 1-3 were found to be 19S, 22R, 24S, 28S, 44S, 45S, 47R, 49S, 53R, 55S, 57S, 59S, 60S, and 63S by application of a modified Mosher's method.

Original languageEnglish
Pages (from-to)783-787
Number of pages5
JournalTetrahedron Letters
Volume54
Issue number8
DOIs
Publication statusPublished - Feb 20 2013
Externally publishedYes

Keywords

  • C-acetonide method
  • JBCA method
  • Stereochemistry
  • Theonezolides A-C
  • Universal NMR database

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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