Modular Syntheses of Phenanthroindolizidine Natural Products

Young In Jo, Martin D. Burke, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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
Pages (from-to)4201-4204
Number of pages4
JournalOrganic Letters
Volume21
Issue number11
DOIs
Publication statusPublished - 2019 Jun 7

Bibliographical note

Funding Information:
This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165, Center for New Directions in Organic Synthesis), and by a grant from the National Institutes of Health, U.S.A. (NIH GM118185) to M.D.B.

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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