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Asymmetric syntheses of diarylheptanoid natural products (−)-centrolobine and (−)-de-O-methylcentrolobine via hetero-Diels–Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]

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Title: Asymmetric syntheses of diarylheptanoid natural products (−)-centrolobine and (−)-de-O-methylcentrolobine via hetero-Diels–Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]
Authors: Washio, Takuya Browse this author
Yamaguchi, Reika Browse this author
Abe, Takumi Browse this author
Nambu, Hisanori Browse this author
Anada, Masahiro Browse this author →KAKEN DB
Hashimoto, Shunichi Browse this author →KAKEN DB
Keywords: diarylheptanoids
hetero-Diels-Alder reaction
(-)-centrolobine
(-)-de-O-methylcentrolobine
chiral Rh(II) catalyst
Issue Date: 26-Nov-2007
Publisher: Elsevier
Journal Title: Tetrahedron
Volume: 63
Issue: 48
Start Page: 12037
End Page: 12046
Publisher DOI: 10.1016/j.tet.2007.09.003
Abstract: Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh_{2}(R-BPTPI)_{4}, as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee.
Relation: http://www.sciencedirect.com/science/journal/00404020
Type: article (author version)
URI: http://hdl.handle.net/2115/32290
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 穴田 仁洋

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