Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade

James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth

doi:10.1021/acs.orglett.0c00053

Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade

James A Rossi-Ashton, Aimee K Clarke, Richard J K Taylor, William P Unsworth

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The polycyclic core of the akuammiline alkaloids can be synthesized from simple tryptamine and tryptophol derivatives via a Ag(I)-catalyzed enantioselective dearomative cyclization cascade sequence. The complex tetracyclic scaffolds are prepared via a rapid, versatile, three-step modular synthesis from simple commercially available indole derivatives in high yields and enantiomeric excess (up to 99% yield and >99% ee).

Original language	English
Pages (from-to)	1175–1181
Number of pages	7
Journal	Organic Letters
Volume	22
Issue number	3
Early online date	15 Jan 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c00053
Publication status	Published - 7 Feb 2020

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10.1021/acs.orglett.0c00053Licence: CC BY

acs.orglett.0c00053
© 2020 American Chemical Society.
Final published version, 1.53 MBLicence: CC BY

Spiroclip Technology: from Catalogue to Spirocycle in One Step
Unsworth, W. P. (Principal investigator) & Taylor, R. J. K. (Co-investigator)
EPSRC
3/04/18 → 30/09/21
Project: Research project (funded) › Research

Cite this

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abstract = "The polycyclic core of the akuammiline alkaloids can be synthesized from simple tryptamine and tryptophol derivatives via a Ag(I)-catalyzed enantioselective dearomative cyclization cascade sequence. The complex tetracyclic scaffolds are prepared via a rapid, versatile, three-step modular synthesis from simple commercially available indole derivatives in high yields and enantiomeric excess (up to 99% yield and >99% ee).",

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AU - Unsworth, William P

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Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade

Abstract

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Projects

Spiroclip Technology: from Catalogue to Spirocycle in One Step

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