113776-06-0Relevant articles and documents
Synthesis and Absolute Configuration of Pyriculol
Suzuki, Masanobu,Sugiyama, Takeyoshi,Watanabe, Masashi,Murayama, Tetsuya,Yamashita, Kyohei
, p. 1121 - 1128 (2007/10/02)
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--6-hydroxybenzaldehyde.