Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

Daniel J. Kerr; Anthony C. Willis; Bernard L. Flynn

doi:10.1021/ol035822q

Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

Daniel J. Kerr, Anthony C. Willis, Bernard L. Flynn^*

^*Corresponding author for this work

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

75 Citations (Scopus)

Abstract

(Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.

Original language	English
Pages (from-to)	457-460
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	4
DOIs	https://doi.org/10.1021/ol035822q
Publication status	Published - 19 Feb 2004

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title = "Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue",

abstract = "(Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.",

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N2 - (Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.

AB - (Equation presented) A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8π-electrocyclization is proposed to explain the formation of this ring-expanded species.

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JO - Organic Letters

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Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

Abstract

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