Furanylidene Systems from a Tosylic Acid- Mediated, Tandem Desilylation-Cyclization Reaction of Silyl Ethers of Monoalkynylated Β -Keto Carbonyls

John Oxford; Rayaj Ahamed; Morgan Hudson-Davis; Brandi Womack; Laura Gessner; Kristina Deveaux; Ebonni Fisher; Karelle S. Aiken

doi:10.1515/HC.2011.044

Furanylidene Systems from a Tosylic Acid- Mediated, Tandem Desilylation-Cyclization Reaction of Silyl Ethers of Monoalkynylated Β -Keto Carbonyls

John Oxford, Rayaj Ahamed, Morgan Hudson-Davis, Brandi Womack, Laura Gessner, Kristina Deveaux, Ebonni Fisher, Karelle S. Aiken

Biochemistry, Chemistry & Physics

Georgia Southern University

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

2 Scopus citations

Abstract

Single isomers of the furanylidene system 8 were synthesized in four steps. The synthesis begins with the dianion of β-keto carbonyls and culminates in a mild, tandem desilylationcyclization reaction using tosylic acid. Compounds synthesized in this study have the potential for further diversification at the alkyne, carbonyl and enol-ether moieties. Hence, the furanylidenes from this study are prospective building blocks for biologically active, furan-containing natural products and their analogs. 2011 ·

Original language	American English
Journal	Heterocyclic Communications
Volume	17
DOIs	https://doi.org/10.1515/HC.2011.044
State	Published - Jan 1 2011

Disciplines

Chemistry
Organic Chemistry

Keywords

Desilylation
Furanylidene
Silyl ether
Tosylic acid

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10.1515/HC.2011.044License: Unspecified

http://dx.doi.org/10.1515/HC.2011.044

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title = "Furanylidene Systems from a Tosylic Acid- Mediated, Tandem Desilylation-Cyclization Reaction of Silyl Ethers of Monoalkynylated Β -Keto Carbonyls",

abstract = "Single isomers of the furanylidene system 8 were synthesized in four steps. The synthesis begins with the dianion of β-keto carbonyls and culminates in a mild, tandem desilylationcyclization reaction using tosylic acid. Compounds synthesized in this study have the potential for further diversification at the alkyne, carbonyl and enol-ether moieties. Hence, the furanylidenes from this study are prospective building blocks for biologically active, furan-containing natural products and their analogs. 2011 ·",

keywords = "Desilylation, Furanylidene, Silyl ether, Tosylic acid",

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T1 - Furanylidene Systems from a Tosylic Acid- Mediated, Tandem Desilylation-Cyclization Reaction of Silyl Ethers of Monoalkynylated Β -Keto Carbonyls

AU - Oxford, John

AU - Ahamed, Rayaj

AU - Hudson-Davis, Morgan

AU - Womack, Brandi

AU - Gessner, Laura

AU - Deveaux, Kristina

AU - Fisher, Ebonni

AU - Aiken, Karelle S.

PY - 2011/1/1

Y1 - 2011/1/1

N2 - Single isomers of the furanylidene system 8 were synthesized in four steps. The synthesis begins with the dianion of β-keto carbonyls and culminates in a mild, tandem desilylationcyclization reaction using tosylic acid. Compounds synthesized in this study have the potential for further diversification at the alkyne, carbonyl and enol-ether moieties. Hence, the furanylidenes from this study are prospective building blocks for biologically active, furan-containing natural products and their analogs. 2011 ·

AB - Single isomers of the furanylidene system 8 were synthesized in four steps. The synthesis begins with the dianion of β-keto carbonyls and culminates in a mild, tandem desilylationcyclization reaction using tosylic acid. Compounds synthesized in this study have the potential for further diversification at the alkyne, carbonyl and enol-ether moieties. Hence, the furanylidenes from this study are prospective building blocks for biologically active, furan-containing natural products and their analogs. 2011 ·

KW - Desilylation

KW - Furanylidene

KW - Silyl ether

KW - Tosylic acid

UR - https://digitalcommons.georgiasouthern.edu/chem-facpubs/5

UR - http://dx.doi.org/10.1515/HC.2011.044

U2 - 10.1515/HC.2011.044

DO - 10.1515/HC.2011.044

M3 - Article

SN - 0793-0283

VL - 17

JO - Heterocyclic Communications

JF - Heterocyclic Communications

ER -

Furanylidene Systems from a Tosylic Acid- Mediated, Tandem Desilylation-Cyclization Reaction of Silyl Ethers of Monoalkynylated Β -Keto Carbonyls

Abstract

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Keywords

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