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

24 October 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

natural product
antibiotics
cycloaddition
cyclopropane

Supplementary materials

Title
Description
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Title
Melokhanine E SI
Description
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