caa a22 4500 475758528 CHVBK 20180406123543.0 cr unu---uuuuu 170329e20000101xx s 000 0 eng 10.1007/BF02499083 doi (NATIONALLICENCE)springer-10.1007/BF02499083 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 ) [Elektronische Daten] [M. Zlokazov, V. Veselovsky] 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. Kluwer Academic/Plenum Publishers, 2000 ( S )-(−)-ethyl lactate nationallicence allylic alcohol nationallicence diastereoselective cyclopropanation nationallicence Julia— Johnson rearrangement nationallicence chiral cyclopropylcarbinol nationallicence (4 S , 5 E )-4-bromomethyl-5-enenitrile nationallicence (10 R )-10-methyltridecan-2-one nationallicence sex pheromone nationallicence southern corn rootworm ( Diabrotica undecimpunctata howardi ) nationallicence Zlokazov M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Veselovsky V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/1(2000-01-01), 154-158 1066-5285 49:1<154 2000 49 11172 https://doi.org/10.1007/BF02499083 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02499083 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Zlokazov M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Veselovsky V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/1(2000-01-01), 154-158 1066-5285 49:1<154 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer