Bridgehead substitution via putative norborn-1-en-3-ones: Application in the synthesis of complex molecules

Faiz Ahmed Khan; Basavaraj M. Budanur; Chava Sudheer

doi:10.1002/chem.201500131

Bridgehead substitution via putative norborn-1-en-3-ones: Application in the synthesis of complex molecules

Faiz Ahmed Khan, Basavaraj M. Budanur, Chava Sudheer

Chemistry (Twin Cities)

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

2 Scopus citations

Abstract

The base-mediated formation of a bridgehead double bond in a bicyclo[2.2.1]heptane system (anit-Bredt molecules) is described. The synthesis of exocyclic norbornyl enones by Wittig reaction of α-diketones is reported. These enones and their Michael adducts are used as substrates for the generation of transient bridgehead enones and their trapping with MeOH and H₂O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products.

Original language	English (US)
Pages (from-to)	7021-7025
Number of pages	5
Journal	Chemistry - A European Journal
Volume	21
Issue number	19
DOIs	https://doi.org/10.1002/chem.201500131
State	Published - Mar 24 2015

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

anti-Bredt
bridgehead alcohols
enones
rearrangements
strained molecules

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10.1002/chem.201500131

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abstract = "The base-mediated formation of a bridgehead double bond in a bicyclo[2.2.1]heptane system (anit-Bredt molecules) is described. The synthesis of exocyclic norbornyl enones by Wittig reaction of α-diketones is reported. These enones and their Michael adducts are used as substrates for the generation of transient bridgehead enones and their trapping with MeOH and H2O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products.",

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T1 - Bridgehead substitution via putative norborn-1-en-3-ones

T2 - Application in the synthesis of complex molecules

AU - Khan, Faiz Ahmed

AU - Budanur, Basavaraj M.

AU - Sudheer, Chava

PY - 2015/3/24

Y1 - 2015/3/24

N2 - The base-mediated formation of a bridgehead double bond in a bicyclo[2.2.1]heptane system (anit-Bredt molecules) is described. The synthesis of exocyclic norbornyl enones by Wittig reaction of α-diketones is reported. These enones and their Michael adducts are used as substrates for the generation of transient bridgehead enones and their trapping with MeOH and H2O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products.

AB - The base-mediated formation of a bridgehead double bond in a bicyclo[2.2.1]heptane system (anit-Bredt molecules) is described. The synthesis of exocyclic norbornyl enones by Wittig reaction of α-diketones is reported. These enones and their Michael adducts are used as substrates for the generation of transient bridgehead enones and their trapping with MeOH and H2O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products.

KW - anti-Bredt

KW - bridgehead alcohols

KW - enones

KW - rearrangements

KW - strained molecules

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JO - Chemistry - A European Journal

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Bridgehead substitution via putative norborn-1-en-3-ones: Application in the synthesis of complex molecules

Abstract

Bibliographical note

Keywords

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