41744-75-6Relevant articles and documents
Identification of sex attractant pheromone components of the tussock moth, Euproctis taiwana (Shiraki) (Lepidoptera: Lymantriidae)
Yasuda,Wakamura,Arakaki
, p. 1813 - 1822 (1995)
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A practical synthesis of long-chain iso-fatty acids (iso-C 12-C19) and related natural products
Richardson, Mark B.,Williams, Spencer J.
supporting information, p. 1807 - 1812 (2013/10/22)
A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C 12-C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12-C14) or the C15 and C16 lactones pentadecanolide (for iso-C 15-C17) and hexadecanolide (for iso-C18-C 19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17 and C18 iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13-C16 and C19 iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.
Dilithium tetrachlorocuprate catalyzed alkylation of aleuritic acid derivatives and synthesis of muscalure
Subramanian,Ahuja, Seema
, p. 724 - 726 (2007/10/03)
Carbon-carbon coupling with the ω-halo or tosyl derivatives of threo-9,10,16-trihydroxyhexadecanoic acid (aleuritic acid) has been carried out in the presence of dilithium tetrachlorocuprate reagent and a short synthesis of muscalure is reported.