Modular Syntheses of Phenanthroindolizidine Natural Products

Young In Jo, Martin Burke, Cheol Hong Cheon

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)4201-4204
Number of pages4
JournalOrganic Letters
Volume21
Issue number11
DOIs
StatePublished - Jun 7 2019

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Boronic Acids
Vanadium
Biological Products
Bromides
Alkaloids
Chlorides
terphenyls
alkaloids
synthesis
products
vanadium
bromides
chlorides
saturation
acids
rings
phenanthroindolizidine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Modular Syntheses of Phenanthroindolizidine Natural Products. / Jo, Young In; Burke, Martin; Cheon, Cheol Hong.

In: Organic Letters, Vol. 21, No. 11, 07.06.2019, p. 4201-4204.

Research output: Contribution to journalArticle

Jo, Young In ; Burke, Martin ; Cheon, Cheol Hong. / Modular Syntheses of Phenanthroindolizidine Natural Products. In: Organic Letters. 2019 ; Vol. 21, No. 11. pp. 4201-4204.
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