Title:
SYNTHESIS OF BIOACTIVE DELTA-LACTONE
Document Type and Number:
Japanese Patent JP3227030
Kind Code:
B2
Abstract:
PURPOSE: To readily synthesize invictolide, i.e., one component of queen- recognition pheromone through a few processes by using diethyl methylmalonate and methacrolein as the starting substances.
CONSTITUTION: Diethyl methylmalonate of formula 1 and methacrolein of formula 2 are condensed in the presence of a base, preferably lithium L-prolinate of formula 3 in a solvent to synthesize an intermediate 4,4-diethoxycarbonyl-2- methylpentanal of formula 4. The intermediate of formula 4 is then reacted with a grignard reagent (e.g. see-amylmagnesium bromide) of formula 5 in a solvent and the resultant diethoxycarbonyl compound of formula 6 is subjected to alkaline hydrolysis. The reaction mixture is subsequently neutralized and the obtained compound of formula 7 is converted into a δ-lactone through a ring closure reaction, thus synthesizing the objective 3,5-dimethyl-6-(1'- methylbutyl)2H-tetrahydropyran-2-one of formula 8.
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Inventors:
Tetsuo Omata
Yoshiichi Tanida
Yoshiichi Tanida
Application Number:
JP16604193A
Publication Date:
November 12, 2001
Filing Date:
June 10, 1993
Export Citation:
Assignee:
NITTO DENKO CORPORATION
International Classes:
B01J31/02; C07B61/00; C07D309/30; C07D315/00; (IPC1-7): C07D309/30; B01J31/02
Domestic Patent References:
| JP6322055A |
Attorney, Agent or Firm:
Yoshihiro Kiyohara