(R)- And (S)-3-methylheneicosan-2-one [(R)- and (S)-I] were prepd. from (R)- and (S)-Br(CH2)3CHMeCO2H [(R)- and (S)-II], resp, in ∼12 steps.  Thus, Me(CH2)12COCH2CO2Me was alkylated by (R)-II and the product was converted to (R)-Me(CH2)12CO(CH2)4CHMeCO2H, which was reduced to (R)-Me(CH2)17CHMeCO2H, which was methylated by MeLi to give (R)-I.

Insect pheromones. Synthesis of both enantiomers of 3-methyl-2-heneicosanone, an analog of the sex pheromone of the German cockroach

ROSSI, RENZO;CARPITA, ADRIANO;
1981

Abstract

(R)- And (S)-3-methylheneicosan-2-one [(R)- and (S)-I] were prepd. from (R)- and (S)-Br(CH2)3CHMeCO2H [(R)- and (S)-II], resp, in ∼12 steps.  Thus, Me(CH2)12COCH2CO2Me was alkylated by (R)-II and the product was converted to (R)-Me(CH2)12CO(CH2)4CHMeCO2H, which was reduced to (R)-Me(CH2)17CHMeCO2H, which was methylated by MeLi to give (R)-I.
Rossi, Renzo; Carpita, Adriano; Marasco, M.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/7387
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