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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]
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)
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Submitter: 穴田 仁洋
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