Absolute configuration of aflastatin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus

Hiroyuki Ikeda, Nobuaki Matsumori, Makoto Ono, Akinori Suzuki, Akira Isogai, Hiromichi Nagasawa, Shohei Sakuda

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Aflastatin A (1) is a specific inhibitor of aflatoxin production by Aspergillus parasiticus. It has the novel structure of a tetramic acid derivative with a long alkyl side chain. The absolute configurations of 29 chiral centers contained in I were chemically elucidated in this study. First, four small fragment molecules were prepared from I or its methyl ether (2), and their absolute structures were assigned as N-methyl-D-alanine, (2S,4R)-2,4-dimethyl-1,6-hexanediol dibenzoate, (R)-3-hydroxydodecanoic acid, and (R)-1,2,4-butanetriol tribenzoate. Next, an acyclic fragment molecule 3 with 13 chiral centers was obtained from I by NaIO4 oxidation, and its relative stereochemistry was elucidated by J-based configuration analysis. By analyzing coupling constants of 3J(H,H) and 2,3J(C,H) and ROE data, the relative configuration of 3 was verified. Finally, by further J-based configuration analysis using a fragment molecule 7 prepared from 2 with 28 chiral carbons, all relative configurations in the alkyl side chain of I were clarified. By connecting these relative configurations with the absolute configurations of first four fragment molecules, the absolute stereochemistry of 1 was fully determined.

Original languageEnglish
Pages (from-to)438-444
Number of pages7
JournalJournal of Organic Chemistry
Volume65
Issue number2
DOIs
Publication statusPublished - Jan 28 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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