Collective Asymmetric Total Synthesis of Cylindricines

17 February 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Collective asymmetric total synthesis of marine tricyclic alkaloids, cylindricines A–H, and the proposed structures of cylindricine I and J, was achieved in a concise manner from a single common spirocyclic pyrrolidine intermediate. A tandem chemoselective oxidation/intramolecular aza-Michael addition/epimerization was exploited to complete the tricyclic skeleton. This work provides a versatile synthetic entry to the cylindricine family of marine tricyclic alkaloids.

Keywords

total synthesis
alkaloids
structure characterization
cytotoxicity
tandem reactions

Supplementary materials

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Description
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Supporting Information
Description
Detailed NMR data of natural and synthetic cylindricines, configurational assignment of important compounds, experimental procedure, compound characterization data, and copies of NMR spectra
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