Synthesis of (R)-Curcumene and (R)-Xanthorrizol Based on 1,2-Aryl Migration via Phenonium Ion

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概要

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• Solvolysis reaction of methyl (4S,5S)-4-(4'-methoxyphenyl)-5-tosyloxy-2(E)-hexenoate 5 in water-saturated MeNO_2 gave the 1,2-migration product, (4S,5S)-5-hydroxy-4-(4'-methoxyphenyl)-2-(E)-hexenoate 6 (55% yield), which was converted to methyl (R)-(4'-methylphenyl)hexanoate 11 in 25% overall yield (5 steps). Treatment of (R)-11 with MeLi gave tertiary alcohol congener 12, which was subjected to dehydration to afford (R)-(-)-curcumene 1. An introduction of hydroxyl group at meta-position of the aromatic ring in (R)-11 was achieved based on consecutive treatment [1) selective iodination, 2) conversion of aryl iodide to aryl boronate, 3) conversion of aryl boronate to phenol]. Thus obtained phenol (R)-16 was treated with MeLi to give tertiary alcohol congener 17, which was subjected to dehydration to afford (R)-(-)-xanthorrizol 2.

• 公益社団法人日本薬学会の論文
• 2007-09-01

著者

• AKITA Hiroyuki

  School of Pharmaceutical Science, Toho University

• Akita H

  Toho Univ. Chiba Jpn

• Akita Hiroyuki

  School Of Pharmaceutical Science Toho University

• ONO Machiko

  School of Pharmaceutical Sciences, Toho University

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• EHARA Takeru

  School of Pharmaceutical Sciences, Toho University

• TANIKAWA Shin

  School of Pharmaceutical Sciences, Toho University

• Ehara Takeru

  School Of Pharmaceutical Sciences Toho University:tsukuba Research Institute Novartis Pharma K.k.

• Tanikawa Shin

  School Of Pharmaceutical Sciences Toho University

• Ono M

  School Of Pharmaceutical Sciences International University Of Health And Welfare

• Ono Machiko

  School Of Pharmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences International Univ. Of Health And Welfare

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