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Published on: April 6, 2019
Modular Syntheses of Phenanthroindolizidine Natural Products
Young-In Jo1, Martin D Burke2, Cheol-Hong Cheon1
1Department of Chemistry , Korea University , 145 Anam-ro , Seongbuk-gu , Seoul 02841 , Republic of Korea.
Abstract:
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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