First asymmetric synthesis of 6-methyl-3-nonanone, the female-produced sex pheromone of the caddisfly Hesperophylax occidentalis
The asymmetric synthesis of the female-produced sex pheromone of the caddisfly Hesperophylax occidentalis, (S)-and (R)-6-methyl-3-nonanone, starting from the simple starting materials propanal, propyl iodide and 2-butanone, in good overall yields is described. The stereogenic centre at the C-6 position of the pheromone was generated via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric induction (ee = 94 and 92%).
Enders,Schuesseler
p. 973 - 975
(2007/10/03)
The total synthesis of (+)-pectinatone: An iterative alkylation approach based on the SAMP-hydrazone method
The marine natural product (+)-pectinatone containing 'skip' 1,3- dimethyl stereocentres was synthesised via the iterative alkylation of propanal SAMP-hydrazone with β-branched iodides. Factors affecting the selectivity of the alkylation reaction and the in situ formation of volatile β-branched iodides are described.
Birkbeck, Anthony A.,Enders, Dieter
p. 7823 - 7826
(2007/10/03)
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