Long-range carbon-proton coupling constants for stereochemical assignment of acyclic structures in natural products: Configuration of the C5-C9 portion of maitotoxin

Nobuaki Matsumori, Taro Nonomura, Makoto Sasaki, Michio Murata, Kazuo Tachibana, Masayuki Satake, Takeshi Yasumoto

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

Long-range carbon-proton coupling constants (2,3J(C,H)) were measured for maitotoxin (MTX), one of the largest natural non-biopolymers, by hetero-half filter experiments and phase-sensitive HMBC with use of 9 mg of a 4% 13C-enriched sample. The necessary coupling constants within the terminal acyclic portions of MTX, where NOE analysis was not successful owing to the presumed coexistence of multiple conformers, were thus obtained for the resultant elucidation of relative configurations for the acyclic stereogenic centers to the 5R*, 7R*, 8R*, and 9S*.

Original languageEnglish
Pages (from-to)1269-1272
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number8
DOIs
Publication statusPublished - Feb 19 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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