(7E,9Z)-Et(CH:CH)2(CH2)nOAc [(7E,9Z)-I (n = 6)], the sex pheromone of Lobesia botrana, was prepd. (21.6%) from EtC≡CBr and MeCH:CH(CH2)6OR (R = tetrahydropyranyl) by sequential cross-coupling reaction [Pd(PPh3)4, MeONa], acetylation (AcOH, reflux, 6 h), and stereoselective redn. [(Me2CHCHMe)2BH, THF].  Similarly, (9Z,11E)-I (n = 8), a sex pheromone component of Spodoptera littoralis, was prepd. (30.2%) from (E)-EtCH:CHI and BrMgC≡C(CH2)8OR (R as before).  (E)-CH2:CHCH:CH(CH2)8OAc, a sex pheromone component of Diparopsis castanea, was prepd. (54.3%) from H2C:CHBr and (Me2CHCHMe)2BCH:CH(CH2)8OR (R as before) by Pd(PPh3)4-catalyzed cross-coupling reaction followed by acetylation (Ac2O, AcOH, 80°).

Synthesis of conjugated and unconjugated 1-alkadienols as candidates for insect attractants

ROSSI, RENZO;CARPITA, ADRIANO;
1981

Abstract

(7E,9Z)-Et(CH:CH)2(CH2)nOAc [(7E,9Z)-I (n = 6)], the sex pheromone of Lobesia botrana, was prepd. (21.6%) from EtC≡CBr and MeCH:CH(CH2)6OR (R = tetrahydropyranyl) by sequential cross-coupling reaction [Pd(PPh3)4, MeONa], acetylation (AcOH, reflux, 6 h), and stereoselective redn. [(Me2CHCHMe)2BH, THF].  Similarly, (9Z,11E)-I (n = 8), a sex pheromone component of Spodoptera littoralis, was prepd. (30.2%) from (E)-EtCH:CHI and BrMgC≡C(CH2)8OR (R as before).  (E)-CH2:CHCH:CH(CH2)8OAc, a sex pheromone component of Diparopsis castanea, was prepd. (54.3%) from H2C:CHBr and (Me2CHCHMe)2BCH:CH(CH2)8OR (R as before) by Pd(PPh3)4-catalyzed cross-coupling reaction followed by acetylation (Ac2O, AcOH, 80°).
Rossi, Renzo; Carpita, Adriano; Quirici, M. G.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/3295
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