Coronafacic acid (1) is an acid component of coronatine, and has been isolated from several pathovars of Pseudomonas syringae. Syntheses of C-6-non- and C-6-alkyl-substituted analogues of 1 were accomplished via intramolecular 1,6-conjugate addition as the key step. Among them, 1 and four C-6-alkyl-substituted analogues exhibited potato tuber-inducing activity, but the C-6-non-substituted analogue did not. It was revealed that a certain length of the C-6-alkyl group was necessary to exhibit activity.
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Hokkaido Univ, Div Fundamental AgriSci Res, Res Fac Agr, Lab Nat Prod Chem, Sapporo, Hokkaido, JapanHokkaido Univ, Div Fundamental AgriSci Res, Res Fac Agr, Lab Nat Prod Chem, Sapporo, Hokkaido, Japan
Miyawaki, Kanji
Inoue, Shiro
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Hokkaido Univ, Div Fundamental AgriSci Res, Res Fac Agr, Lab Nat Prod Chem, Sapporo, Hokkaido, JapanHokkaido Univ, Div Fundamental AgriSci Res, Res Fac Agr, Lab Nat Prod Chem, Sapporo, Hokkaido, Japan
Inoue, Shiro
Kitaoka, Naoki
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Hokkaido Univ, Div Fundamental AgriSci Res, Res Fac Agr, Lab Nat Prod Chem, Sapporo, Hokkaido, JapanHokkaido Univ, Div Fundamental AgriSci Res, Res Fac Agr, Lab Nat Prod Chem, Sapporo, Hokkaido, Japan