Reaction of diketene with Grignard reagents in the presence of cobalt catalyst. A convenient method for the synthesis of 3-methylenealkanoic acids leading to terpenoids.

スポンサーリンク

概要

• 論文の詳細を見る

• Primary alkyl Grignard reagents react regioselectively with diketene in the presence of cobalt(II) iodide to afford 3-methylenealkanoic acids in good yields. The synthetic utility of this reaction is demonstrated in the syntheses of terpenoids by two methods. Utilizing the isomerization of double bond of 3-methylenealkanoic acids, geranic acid and farnesic acid were obtained in two steps. Another method, the tandem [3,3] sigmatropic rearrangement of the corresponding allylic esters was used for the synthesis of C<SUB>18</SUB>-Cecropia juvenile hormone.

• 公益社団法人 日本化学会の論文

著者

• Fujisawa Tamotsu

  Chemistry Department Of Resources Mie University

• Sato Toshio

  Chemistry Department Of Resources Mie University

• SATO Toshio

  Chemistry Department of Resources, MIE UNIVERSITY

• Kawara Tatsuo

  Chemistry Department of Resources, Mie University

• Kawashima Masatoshi

  Chemistry Department of Resources, Mie University

• Gotoh Yoshihiko

  Chemistry Department of Resources, Mie University

関連論文

• PB145 ASYMMETRIC SYNTHESIS OF (-)-MALYNGOLIDE AND (-)-FRONTALIN BY UTILIZING BAKERS' YEAST REDUCTION OF S-ETHYL 2-CYCLOPENTANONECARBOXYLTHIOATE
• Reaction of diketene with Grignard reagents in the presence of cobalt catalyst. A convenient method for the synthesis of 3-methylenealkanoic acids leading to terpenoids.
• A facile method for the preparation of .GAMMA.-alkenyl-.GAMMA.-butyrolactones.
• Regio- and stereoselective ring opening of .OMEGA.-alkenyllactones using organocopper reagents.
• A general method for the synthesis of both enantiomers of optically pure .BETA.-hydroxy esters from (S)-(p-chlorophenylsulfinyl)acetone easily obtainable by kinetic resolution with bakers' yeast.
• Preparation of optically pure .ALPHA.-alkyl .BETA.-hydroxy nitriles by the bakers' yeast reduction.
• One-step synthesis of long-chain aliphatic .ALPHA.,.OMEGA.-dicarboxylic acids utilizing the copper-catalyzed reaction of .BETA.-propiolactone with .ALPHA.,.OMEGA.-di-Grignard reagents.
• Jasmonoid synthesis from cis-4-heptenoic acid.
• One-pot synthesis of acid anhydrides from acids using N,N,N',N'-tetramethylchloroformamidinium chloride under mild conditions.
• A simple method for the synthesis of exaltolide.

スポンサーリンク