An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical co-oxygenation of thiols and monoterpenes

Edward E. Korshin; Roland Hoos; Alex M. Szpilman; Leonid Konstantinovski; Gary H. Posner; Mario D. Bachi

doi:10.1016/s0040-4020(02)00126-6

An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical co-oxygenation of thiols and monoterpenes

Edward E. Korshin, Roland Hoos, Alex M. Szpilman, Leonid Konstantinovski, Gary H. Posner, Mario D. Bachi

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

48 Scopus citations

Abstract

Synthesis of β-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. β-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to β-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described.

Original language	English
Pages (from-to)	2449-2469
Number of pages	21
Journal	Tetrahedron
Volume	58
Issue number	12
DOIs	https://doi.org/10.1016/s0040-4020(02)00126-6
State	Published - 18 Mar 2002
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by grant No. 94-102 from the United States—Israel Binational Science Foundation (BSF), Jerusalem, Israel. E. E. K. and L. K. are grateful to the Israel Ministry of Absorption for financial support. R. H. thanks the Swiss Society of the Friends of the Weizmann Institute of Science for a generous fellowship. We gratefully acknowledge Dr L. Shimon for X-ray analysis.

Funding

This research was supported by grant No. 94-102 from the United States—Israel Binational Science Foundation (BSF), Jerusalem, Israel. E. E. K. and L. K. are grateful to the Israel Ministry of Absorption for financial support. R. H. thanks the Swiss Society of the Friends of the Weizmann Institute of Science for a generous fellowship. We gratefully acknowledge Dr L. Shimon for X-ray analysis.

Funders	Funder number
Israel Ministry of Absorption
Swiss Society of the Friends of the Weizmann Institute of Science
United States-Israel Binational Science Foundation
United States-Israel Binational Science Foundation

Keywords

Antimalarial peroxides
Free radicals
Multi-component reaction
Sequential reactions
Thiol olefin co-oxygenation reaction

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10.1016/s0040-4020(02)00126-6

Cite this

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title = "An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical co-oxygenation of thiols and monoterpenes",

abstract = "Synthesis of β-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. β-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to β-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described.",

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author = "Korshin, {Edward E.} and Roland Hoos and Szpilman, {Alex M.} and Leonid Konstantinovski and Posner, {Gary H.} and Bachi, {Mario D.}",

note = "Funding Information: This research was supported by grant No. 94-102 from the United States—Israel Binational Science Foundation (BSF), Jerusalem, Israel. E. E. K. and L. K. are grateful to the Israel Ministry of Absorption for financial support. R. H. thanks the Swiss Society of the Friends of the Weizmann Institute of Science for a generous fellowship. We gratefully acknowledge Dr L. Shimon for X-ray analysis.",

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doi = "10.1016/s0040-4020(02)00126-6",

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AU - Konstantinovski, Leonid

AU - Posner, Gary H.

AU - Bachi, Mario D.

N1 - Funding Information: This research was supported by grant No. 94-102 from the United States—Israel Binational Science Foundation (BSF), Jerusalem, Israel. E. E. K. and L. K. are grateful to the Israel Ministry of Absorption for financial support. R. H. thanks the Swiss Society of the Friends of the Weizmann Institute of Science for a generous fellowship. We gratefully acknowledge Dr L. Shimon for X-ray analysis.

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N2 - Synthesis of β-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. β-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to β-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described.

AB - Synthesis of β-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. β-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to β-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described.

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An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical co-oxygenation of thiols and monoterpenes

Abstract

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