Synthesis of the honey-bee attractant 13-hydroxy-2-oxotridecane

13-Hvdroxy-2-oxotridecane, which is isolated from extract of Evodia hupehensis Dode honey-bee eggs and actively attracts honey bees, is synthesized via ozonolysis of 1-methylcyclododecene and tetradec-13-en-2-one, the product from monoalkylation of the acetoacetic ester with 1-bromo-10-undecene foll...

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Bibliographic Details
Published inChemistry of natural compounds Vol. 37; no. 2; pp. 190 - 192
Main Authors Ishmuratov, GY, Yakovleva, MP, Kharisov, RY, Botsman, OV, Izibairov, OI, Mannapov, AG, Tolstikov, GA
Format Journal Article
LanguageEnglish
Published NEW YORK CONSULTANTS BUREAU 01.03.2001
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
synthesis
1-methylcyclododecene
ozonolysis
bee
sodium triacetoxyborohydride
tetradec-13-en-2-one
acetoacetic ester
13-hydroxy-2-oxotridecane
1-bromo-10-undecene
bee attractant
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Summary:13-Hvdroxy-2-oxotridecane, which is isolated from extract of Evodia hupehensis Dode honey-bee eggs and actively attracts honey bees, is synthesized via ozonolysis of 1-methylcyclododecene and tetradec-13-en-2-one, the product from monoalkylation of the acetoacetic ester with 1-bromo-10-undecene followed by decarbethoxylation, with further reduction of the intermediate peroxides using NaBH(OAc)(3).
ISSN:0009-3130
DOI:10.1023/A:1012351524532