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Stereocontrolled Synthesis of Melokhanine E via an Intramolecular Formal [3+2] Cycloaddition

preprint
submitted on 22.10.2019 and posted on 24.10.2019 by Joshua Pierce, Anna Cholewczynski, Peyton Williams

A convergent sequence to access the indole alkaloid melokhanine E in 12-steps (8-step longest linear sequence) and an 11% overall yield is reported. The approach utilizes two cyclopropane moieties as reactive precursors to a 1,3-dipole and imine species to enable stereoselective construction of the core scaffold through a formal [3+2] cycloaddition. The natural product was evaluated for its antimicrobial activity based on isolation reports; however, no activity was observed. The reported efforts serve as a synthetic platform to prepare an array of alkaloids bearing this core structural motif.

Funding

NIGMS (R01GM117570)

History

Email Address of Submitting Author

jgpierce@ncsu.edu

Institution

NC State University

Country

United States

ORCID For Submitting Author

0000-0001-9194-3765

Declaration of Conflict of Interest

The authors declare no conflicts of interest.

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