ol9b01397_si_001.pdf (2.28 MB)
Modular Syntheses of Phenanthroindolizidine Natural Products
journal contribution
posted on 2019-05-21, 11:34 authored by Young-In Jo, Martin D. Burke, Cheol-Hong CheonA 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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strategyhexahydroindolizinePhenanthroSubsequent saturationbromoaryl Nalkaloidsmesyl chlorideSuzukidihydroindolizidinium ringphenanthrosynthesisNaturalmethyliminodiacetatepyridyl bromideone-potaryl boronic acidsaza-terphenylvanadium-catalyzed oxidative electrocyclizationcolumn-separation operationsiterativeMIDAorthoModular Synthesesboronatebond
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