Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts

Masaki Kamata; Motoko Ohta; Ken Ichi Komatsu; Hye Sook Kim; Yusuke Wataya

doi:10.1016/S0040-4039(02)00166-1

Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts

Masaki Kamata, Motoko Ohta, Ken Ichi Komatsu, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journal › Article

17 Citations (Scopus)

Abstract

1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC₆H₄, 1b: Ar=Ph, 1c: Ar=p-MeC₆H₄, 1d: Ar=p-MeOC₆H₄) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr₂ were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.

Original language	English
Pages (from-to)	2063-2067
Number of pages	5
Journal	Tetrahedron Letters
Volume	43
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(02)00166-1
Publication status	Published - Mar 11 2002

Keywords

1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes
Antimalarial activity
Cyclic peroxides
FeBr
Fragmentation
O-1,2-aryl shift
Reaction mechanism
Rearrangement

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts",

abstract = "1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.",

keywords = "1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes, Antimalarial activity, Cyclic peroxides, FeBr, Fragmentation, O-1,2-aryl shift, Reaction mechanism, Rearrangement",

author = "Masaki Kamata and Motoko Ohta and Komatsu, {Ken Ichi} and Kim, {Hye Sook} and Yusuke Wataya",

year = "2002",

month = mar,

day = "11",

doi = "10.1016/S0040-4039(02)00166-1",

language = "English",

volume = "43",

pages = "2063--2067",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

number = "11",

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T1 - Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes

T2 - Direct evidence for nucleophilic O-1,2-aryl shifts

AU - Kamata, Masaki

AU - Ohta, Motoko

AU - Komatsu, Ken Ichi

AU - Kim, Hye Sook

AU - Wataya, Yusuke

PY - 2002/3/11

Y1 - 2002/3/11

N2 - 1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.

AB - 1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.

KW - 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes

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KW - Reaction mechanism

KW - Rearrangement

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