Organic Letters p. 4201 - 4204 (2019)
Update date:2022-08-04
Topics: Functionalization Stereochemistry Total synthesis Building blocks Protecting groups Organic synthesis Spectroscopic data Catalysis Analytical Techniques Reaction Optimization Chiral synthesis Purification techniques Modular syntheses Natural Product Isolation
Jo, Young-In
Burke, Martin D.
Cheon, Cheol-Hong
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.
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