Modular Syntheses of Phenanthroindolizidine Natural Products
A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.
Jo, Young-In,Burke, Martin D.,Cheon, Cheol-Hong
p. 4201 - 4204
(2019/06/14)
Synthesis of tylocrebrine and related phenanthroindolizidines by VOF 3-mediated oxidative aryl-alkene coupling
A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.
Niphakis, Micah J.,Georg, Gunda I.
p. 196 - 199
(2011/03/19)
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