Ground state oxygen in synthesis of cyclic peroxides. Part 1: Benzo fused ketals

Junwon Kim; Hong Bin Li; Andrew S. Rosenthal; Dongpei Sang; Theresa A. Shapiro; Mario D. Bachi; Gary H. Posner

doi:10.1016/j.tet.2006.02.008

Ground state oxygen in synthesis of cyclic peroxides. Part 1: Benzo fused ketals

Junwon Kim, Hong Bin Li, Andrew S. Rosenthal, Dongpei Sang, Theresa A. Shapiro, Mario D. Bachi, Gary H. Posner

School of Medicine

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

21 Scopus citations

Abstract

A thiol-olefin-cooxygenation (TOCO) radical chain reaction involving ground state molecular oxygen converts 2′-isopropenyl acetophenones directly into cyclic peroxy hemiketal products with three new bonds. Starting with 4-t-butylbenzenethiol, this TOCO process proceeds reproducibly on gram scale in 86% yield. Hemiketal→ketal and sulfide→sulfone transformations finally provide a series of sulfonyl cyclic peroxy ketals. The in vitro antimalarial activities of some of these structurally simple benzo-fused cyclic peroxides are reported.

Original language	English (US)
Pages (from-to)	4120-4127
Number of pages	8
Journal	Tetrahedron
Volume	62
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2006.02.008
State	Published - Apr 24 2006

Keywords

Endoperoxides
Malaria
Molecular oxygen
Radical oxygenation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.02.008

Cite this

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title = "Ground state oxygen in synthesis of cyclic peroxides. Part 1: Benzo fused ketals",

abstract = "A thiol-olefin-cooxygenation (TOCO) radical chain reaction involving ground state molecular oxygen converts 2′-isopropenyl acetophenones directly into cyclic peroxy hemiketal products with three new bonds. Starting with 4-t-butylbenzenethiol, this TOCO process proceeds reproducibly on gram scale in 86% yield. Hemiketal→ketal and sulfide→sulfone transformations finally provide a series of sulfonyl cyclic peroxy ketals. The in vitro antimalarial activities of some of these structurally simple benzo-fused cyclic peroxides are reported.",

keywords = "Endoperoxides, Malaria, Molecular oxygen, Radical oxygenation",

author = "Junwon Kim and Li, {Hong Bin} and Rosenthal, {Andrew S.} and Dongpei Sang and Shapiro, {Theresa A.} and Bachi, {Mario D.} and Posner, {Gary H.}",

note = "Funding Information: We thank the NIH (AI-34885 and RR00052) for financial support and Suji Xie for help with the in vitro antimalarial testing, and Dr. Amy Sarjeant for the X-ray crystallography.",

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language = "English (US)",

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T1 - Ground state oxygen in synthesis of cyclic peroxides. Part 1

T2 - Benzo fused ketals

AU - Kim, Junwon

AU - Li, Hong Bin

AU - Rosenthal, Andrew S.

AU - Sang, Dongpei

AU - Shapiro, Theresa A.

AU - Bachi, Mario D.

AU - Posner, Gary H.

N1 - Funding Information: We thank the NIH (AI-34885 and RR00052) for financial support and Suji Xie for help with the in vitro antimalarial testing, and Dr. Amy Sarjeant for the X-ray crystallography.

PY - 2006/4/24

Y1 - 2006/4/24

N2 - A thiol-olefin-cooxygenation (TOCO) radical chain reaction involving ground state molecular oxygen converts 2′-isopropenyl acetophenones directly into cyclic peroxy hemiketal products with three new bonds. Starting with 4-t-butylbenzenethiol, this TOCO process proceeds reproducibly on gram scale in 86% yield. Hemiketal→ketal and sulfide→sulfone transformations finally provide a series of sulfonyl cyclic peroxy ketals. The in vitro antimalarial activities of some of these structurally simple benzo-fused cyclic peroxides are reported.

AB - A thiol-olefin-cooxygenation (TOCO) radical chain reaction involving ground state molecular oxygen converts 2′-isopropenyl acetophenones directly into cyclic peroxy hemiketal products with three new bonds. Starting with 4-t-butylbenzenethiol, this TOCO process proceeds reproducibly on gram scale in 86% yield. Hemiketal→ketal and sulfide→sulfone transformations finally provide a series of sulfonyl cyclic peroxy ketals. The in vitro antimalarial activities of some of these structurally simple benzo-fused cyclic peroxides are reported.

KW - Endoperoxides

KW - Malaria

KW - Molecular oxygen

KW - Radical oxygenation

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JO - Tetrahedron

JF - Tetrahedron

IS - 17

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Ground state oxygen in synthesis of cyclic peroxides. Part 1: Benzo fused ketals

Abstract

Keywords

ASJC Scopus subject areas

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