Synthesis and Absolute Configuration of Pyriculol
1987 年 51 巻 4 号 p. 1121-1127
詳細
1987 年 51 巻 4 号 p. 1121-1127
A total synthesis of optically active pyriculol is described. The Wittig reaction between an aldehyde 19 and a triphenylphosphonium ylide 12 gave an intermediate 20. Successive treatment of 20 with p-toluenesulfonic acid, active manganese dioxide, and potassium carbonate gave (3'R, 4'S)-pyriculol (23), which was identical with natural pyriculol (1) in all respects. From this synthesis, the absolute stereochemistry of pyriculol (1) was determined to be 2-[(3'R, 4'S')-3/, 4'-dihydroxy(1'E, 5'E)-1', 5'-heptadienyl]-6-hydroxybenzaldehyde.
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