A new stereoselective synthesis of (Z)-9-tricosene, the sex attractant of the common housefly
Muscalure (9/tricosene) was prepd. very readily by an instant-ylid reaction of nonanal with Ph3P:CH(CH2)12Me or of (Z)-Me(CH2)7CH:CHCH2OAc with BrMg(CH2)11Me. (Z)-9-Tricosene was formed in a highly selective manner (.apprx.97.5) although it was difficult to assess the Z/E-ratio with accuracy. [on SciFinder (R)]
1985
26
3
305
6
CAN 103:6066
26-2
Biomolecules and Their Synthetic Analogs
N.D. Zelinskii Inst. Org. Chem.,Moscow,USSR.
Journal
written in English.
143-15-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with undecenylacetate); 821-95-4 Role: RCT (Reactant), RACT (Reactant or reagent) (acetoxylation of); 96854-02-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with dodecylmagnesium bromide); 96854-01-2; 96854-03-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with nonanal); 124-19-6; 27519-02-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with triphenylphosphoniotetradecylide)
REVIEWED
EPFL