As the key compound for the construction of cisoid terpenoids, (2Z ,6Z)-8-benzyloxy-1-chloro-2,6-dimethylocta-2,6-diene was synthesized stereoselectively via the Wittig reaction starting from nerol. The ten-carbon building block was coupled with prenyl or neryl p-tolyl sulfone to afford, after reductive desulfonylation, (Z,Z)-farnesol and (Z,Z,Z) -nerylnerol, respectively.
A stereospecific synthesis of 1-acetoxy-5-bromo-2-methyl-2-cis-pentene in 4 steps starting from 3-formyl-5,6-dihydro-2H-pyran, dimer of acrolein, followed by alkylation of 2-ethoxycarbonyl-3-methylbicyclo[2.2.1]hept-2-ene with the bromide furnished a facile synthesis of (±)-β-santalol.
The reaction of several organic halides with the complexes, prepared from 1-bromo-2-methyl-4-phenoxy-2-butene or 4-benzyloxy-1-bromo-2-methyl-2-butene and nickel carbonyl in benzene, afforded trisubstituted (E)-olefins, such as 2-methyl-4-phenoxy-1-phenyl-2-butene, geranyl benzyl ether, and farnesyl benzyl ether, stereoselectively.
The reaction of 2,6-dibromocyclohexanone (1)with morpholine gives 1-cyclopentenecarboxymorpholide (2) and 2-morpholino-2-cyclohexenone (3) . The ratio of 2 :3 is remarkably affected by the reaction solvent, and the amide 2 or the enaminoketone 3 is obtained selectively when chloroform or HMPA was used, respectively.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.