Synthetic Study of Piericidins. II. Synthesis of Piericidin Analogues

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概要

• 論文の詳細を見る

• Two piericidin analogues having a simple aromatic ring were synthesized based on a palladium-catalyzed cross-coupling reaction and the reaction of sulfone and aldehyde by the Julia coupling procedure. The reaction of 3-methoxyphenyl-tri-n-butyltin (8) and a mixture of allylic chlorides ((E)-9 and (Z)-10) in the presence of tetrakis(triphenylphosphine) palladium(0) afforded a mixture of 5-arylacetals (E)-11 and (Z)-12. The coupling reaction of the non-conjugated aldehyde (E)-13 or (Z)-14 prepared from the 5-arylacetal (E)-11 or (Z)-12 and the sulfone 4 provided (2E)-19 or (2Z)-20. Benzoylation of (2E)-19 or (2Z)-20 followed by reductive olefin-formation with sodium amalgam gave the piericidin analogue (2E)-1 or (2Z)-2. Analogue (2E)-1 has the same side chain as natural piericidin and analogue 2 is the (2Z)-isomer of analogue 1 at the side chain.

• 公益社団法人日本薬学会の論文
• 1997-11-15

著者

• Ono Mayumi

  Department Of Pharmaceutical Oncology Graduate School Of Pharmaceutical Sciences Kyushu University

• Ono M

  Departments Of Biochemistry Kyushu University School Of Medicine

• Ono M

  Kyushu Tokai Univ. Kumamoto Jpn

• AKITA Hiroyuki

  School of Pharmaceutical Science, Toho University

• Yoshida Naoko

  Institute For Medical And Dental Engineering Tokyo Medical And Dental University

• Akita H

  Toho Univ. Chiba Jpn

• Akita Hiroyuki

  School Of Pharmaceutical Science Toho University

• 吉田 直之

  大日本製薬株式会社創薬研究所第一薬理研究部

• Ono M

  Analytical Laboratory Self-medication Laboratories Taisho Pharmaceutical Co. Ltd.

• Yoshida Naotoshi

  Medicinal Plant Garden Faculty Of Pharmaceutical Sciences Hokkaido University

• Ono Masaki

  Analytical Laboratory Self-medication Laboratories Taisho Pharmaceutical Co. Ltd.

• 吉田 直之

  大日本製薬株式会社創薬研究所

• ONO Machiko

  School of Pharmaceutical Sciences, Toho University

• YOSHIDA Norio

  School of Pharmaceutical Sciences, Toho University

• Ono M

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences International Univ. Of Health And Welfare

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