A Rapid Synthetic Approach to the ABCD Core of the Stemona Alkaloids

Rickki Connelly; Jonathan Knowles; Kevin Booker-Milburn

doi:10.1021/acs.orglett.8b03371

A Rapid Synthetic Approach to the ABCD Core of the Stemona Alkaloids

Rickki Connelly, Jonathan Knowles, Kevin Booker-Milburn^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

A new Lewis acid-assisted Brønsted acid cascade approach for the stereoselective formation of the tetracyclic Stemona alkaloid skeleton is described in five steps from epoxide 15. Crucially, this tetracyclic product can be accessed as either C13 epimer, potentially serving as intermediates for the synthesis of a range of Stemona alkaloids.

Original language	English
Pages (from-to)	18-21
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	1
Early online date	18 Dec 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b03371
Publication status	Published - 4 Jan 2019

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BCS and TECS CDTs

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/acs.orglett.8b03371 . Please refer to any applicable terms of use of the publisher.
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abstract = "A new Lewis acid-assisted Br{\o}nsted acid cascade approach for the stereoselective formation of the tetracyclic Stemona alkaloid skeleton is described in five steps from epoxide 15. Crucially, this tetracyclic product can be accessed as either C13 epimer, potentially serving as intermediates for the synthesis of a range of Stemona alkaloids.",

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AB - A new Lewis acid-assisted Brønsted acid cascade approach for the stereoselective formation of the tetracyclic Stemona alkaloid skeleton is described in five steps from epoxide 15. Crucially, this tetracyclic product can be accessed as either C13 epimer, potentially serving as intermediates for the synthesis of a range of Stemona alkaloids.

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M3 - Article (Academic Journal)

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JO - Organic Letters

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A Rapid Synthetic Approach to the ABCD Core of the Stemona Alkaloids

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