A novel polyfunctional chiral building block derived from (S)-ethyl lactate. Application to the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi) |
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Authors: | M V Zlokazov and V V Veselovsky |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation |
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Abstract: | Highly enantiomerically pure (4S, 5E)-4-bromomethylhept-5-enenitrile was prepared from (S)-ethyl lactate by a six-step procedure involving a rearrangement of chiral cyclopropylcarbinol. This product was used for
the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi), (10R)-10-methyltridecan-2-one.
For preliminary communication, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 151–155, January, 2000. |
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Keywords: | (S)-(− )-ethyl lactate allylic alcohol diastereoselective cyclopropanation Julia— Johnson rearrangement chiral cyclopropylcarbinol (4S 5E)-4-bromomethyl-5-enenitrile (10R)-10-methyltridecan-2-one sex pheromone southern corn rootworm (Diabrotica undecimpunctata howardi) |
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