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

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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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10.1021/acs.orglett.8b03371

Org Lett 2019 - author acceptedAccepted author manuscript, 711 KB

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title = "A Rapid Synthetic Approach to the ABCD Core of the Stemona Alkaloids",

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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N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/85059640319

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DO - 10.1021/acs.orglett.8b03371

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JO - Organic Letters

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

Abstract

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