Total Synthesis of Phenanthroquinolizidine Alkaloids Using a Building Block Strategy

Young In Jo, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A concise and general strategy for the total synthesis of the phenanthroquinolizidine alkaloids has been developed. An iterative Suzuki-Miyaura coupling reaction between the requisite aryl boronic acid, 2-bromo-4,5-dimethoxyphenyl N-methyliminodiacetate (MIDA) boronate derived from boronic acid, and a suitable bromopyridine substrate bearing a homopropargyl alcohol at the 2-position generated the desired ortho-aza-terphenyl compounds. Hydrogenation of the triple bond followed by treatment with methanesulfonyl chloride afforded their corresponding tetrahydroquinolizinium ion intermediates, which were subsequently reacted with NaBH4 to provide the desired hexahydroquinolizine products. A final oxidative electrocyclization reaction gave the target phenanthroquinolizidine natural products. This synthetic approach only requires the use of three chromatographic separations throughout the entire synthesis.

Original languageEnglish
Pages (from-to)11902-11910
Number of pages9
JournalJournal of Organic Chemistry
Volume84
Issue number18
DOIs
Publication statusPublished - 2019 Sept 20

Bibliographical note

Funding Information:
This work was supported by the 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).

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus subject areas

  • Organic Chemistry

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