524695-45-2Relevant academic research and scientific papers
Synthesis of naturally occurring pyridine alkaloids via palladium-catalyzed coupling/migration chemistry
Wang, Yao,Dong, Xiaoyang,Larock, Richard C.
, p. 3090 - 3098 (2007/10/03)
The palladium-catalyzed cross-coupling of 3-iodopyridine, long-chain terminal dienes, and benzylic amines or tosylamides provides a novel route to key intermediates for the synthesis of the naturally occurring, biologically active pyridine alkaloids theonelladins C and D, niphatesine C, and xestamine D. This process involves (1) oxidative addition of the heterocyclic iodide to Pd(0), (2) carbopalladation of the least hindered carbon-carbon double bond of the diene, (3) palladium migration, and (4) π-allylpalladium displacement by the nitrogen nucleophile with simultaneous regeneration of the Pd catalyst. Subsequent hydrogenation and deprotection affords good yields of the natural products. The Pd-catalyzed coupling of 3-iodopyridine and 2-methyl-11-dodecen-1-ol provides a convenient synthesis of a long-chain aldehyde by an analogous palladium migration process, which is easily converted to the pyridine alkaloid ikimine A.
Synthesis of pyridine alkaloids via Pd-catalyzed coupling of 3-iodopyridine, 1,ω-dienes and nitrogen nucleophiles
Larock, Richard C,Wang, Yao
, p. 21 - 23 (2007/10/03)
The palladium-catalyzed cross coupling of 3-iodopyridine, long chain 1,ω-dienes, and benzylic amines or tosylamides provides a novel route to key intermediates for the synthesis of the naturally occurring, biologically active pyridine alkaloids theonellad
