期刊
TETRAHEDRON-ASYMMETRY
卷 17, 期 21, 页码 2976-2980出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2006.11.005
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The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.
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