Unsaturated malonyl esters underwent Pd-catalyzed intramolecular allylic alkylation to give 4-vinyl-substituted gamma-lactones. In contrast to the formerly studied cyclization of malonamides, this reaction could be achieved only with a substrate incorporating a suitably positioned silicon moiety, which directs the ionization toward the desired eta(3)-allyipalladium complex. The resulting 4-[dimethyl-(2-thienyl)silylvinyl]lactone could be subsequently engaged into Hiyama couplings with various iodoarenes, to give the corresponding 4-(alpha-styryl)-gamma-lactones. The use of a specifically substituted iodoarene generated an advanced tetracyclic lactone intermediate incorporating rings A-D of lignans belonging to the podophyllotoxin family. Subsequent electrophilic aromatic substitution with a variety of electron-rich arenes afforded the target picropodophyllin analogs.
机构:
Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
Boglio, C
;
Stahlke, S
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Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
Stahlke, S
;
Thorimbert, S
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Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
Thorimbert, S
;
Malacria, M
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Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
机构:
Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, SwedenKarolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Colon, Eugenia
;
Zaman, Farasat
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机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Zaman, Farasat
;
Axelson, Magnus
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机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Axelson, Magnus
;
Larsson, Olle
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机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Larsson, Olle
;
Carlsson-Skwirut, Christine
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机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Carlsson-Skwirut, Christine
;
Svechnikov, Konstantin V.
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机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Svechnikov, Konstantin V.
;
Soder, Olle
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机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
机构:
Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
Boglio, C
;
Stahlke, S
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h-index: 0
机构:
Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
Stahlke, S
;
Thorimbert, S
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h-index: 0
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Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
Thorimbert, S
;
Malacria, M
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机构:
Univ Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, FranceUniv Paris 06, UMR CNRS 7611, Chim Organ Lab, Inst Chim Mol, F-75005 Paris, France
机构:
Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, SwedenKarolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Colon, Eugenia
;
Zaman, Farasat
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h-index: 0
机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Zaman, Farasat
;
Axelson, Magnus
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h-index: 0
机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Axelson, Magnus
;
Larsson, Olle
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h-index: 0
机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Larsson, Olle
;
Carlsson-Skwirut, Christine
论文数: 0引用数: 0
h-index: 0
机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Carlsson-Skwirut, Christine
;
Svechnikov, Konstantin V.
论文数: 0引用数: 0
h-index: 0
机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden
Svechnikov, Konstantin V.
;
Soder, Olle
论文数: 0引用数: 0
h-index: 0
机构:Karolinska Inst, Astrid Lindgren Childrens Hosp, Dept Woman & Child Hlth, Paediat Endocrinol Unit, S-17176 Stockholm, Sweden