Synthesis of spirocyclic gamma-lactones by cascade beckwith-dowd ring expansion/cyclization

Judith Hierold; David Lupton

doi:10.1021/ol301386k

Synthesis of spirocyclic gamma-lactones by cascade beckwith-dowd ring expansion/cyclization

Judith Hierold, David Lupton

School of Chemistry

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

29 Citations (Scopus)

Abstract

A range of spirocyclic gamma-lactones have been prepared exploiting a Beckwith-Dowd ring expansion cascade involving 1-, 3-, 4-, and 5-carbon expansion of cyclopentanone and cyclohexanone followed by 5-exo-trig or 5-exo-dig cyclization. This radical cascade reaction can be achieved with various substrates to provide a broad range of gamma-lactones spirofused to 6- to 10-membered cycloalkanones.

Original language	English
Pages (from-to)	3412 - 3415
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	13
DOIs	https://doi.org/10.1021/ol301386k
Publication status	Published - 2012

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10.1021/ol301386k

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title = "Synthesis of spirocyclic gamma-lactones by cascade beckwith-dowd ring expansion/cyclization",

abstract = "A range of spirocyclic gamma-lactones have been prepared exploiting a Beckwith-Dowd ring expansion cascade involving 1-, 3-, 4-, and 5-carbon expansion of cyclopentanone and cyclohexanone followed by 5-exo-trig or 5-exo-dig cyclization. This radical cascade reaction can be achieved with various substrates to provide a broad range of gamma-lactones spirofused to 6- to 10-membered cycloalkanones.",

author = "Judith Hierold and David Lupton",

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journal = "Organic Letters",

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AU - Lupton, David

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AB - A range of spirocyclic gamma-lactones have been prepared exploiting a Beckwith-Dowd ring expansion cascade involving 1-, 3-, 4-, and 5-carbon expansion of cyclopentanone and cyclohexanone followed by 5-exo-trig or 5-exo-dig cyclization. This radical cascade reaction can be achieved with various substrates to provide a broad range of gamma-lactones spirofused to 6- to 10-membered cycloalkanones.

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DO - 10.1021/ol301386k

M3 - Article

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SP - 3412

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JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Synthesis of spirocyclic gamma-lactones by cascade beckwith-dowd ring expansion/cyclization

Abstract

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