Total synthesis of Male Dried Bean Beetle Sex Pheromone:
| Reference: | Kocienski, P.; Cernogliaro, G.; Feldstein, G. J. Org. Chem. 1977, 42, 353. DOI |
| Reactions: | Claisen-Johnson - Propargyl-OH • Allene synthesis • Selenoxide-Ei → EnoateEster • CarboxEster → EnoateEster • Mg-Alkyl+CO2 • Alkyl-OH → Alkyl-Br • Appel → Br • CarboxEster → Alkyl-OH • CarboxEster → CarboxEster-α-SeR • Fischer esterification • |
| Reagents: | Orthoacetate • AlHiBu2 • PPh3, CBr4 • Alkyl-MgX • Alkyl-MgX • CO2 • HOMe (react) • LiNiPr2 • Diselenide, phenyl • Periodate, sodium • AlH4-Li+ • |