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Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L

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Title: Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L
Authors: Washio, Takuya Browse this author
Nambu, Hisanori Browse this author →KAKEN DB
Anada, Masahiro Browse this author →KAKEN DB
Hashimoto, Shunichi Browse this author →KAKEN DB
Issue Date: 22-Oct-2007
Publisher: Elsevier
Journal Title: Tetrahedron Asymmetry
Volume: 18
Issue: 21
Start Page: 2606
End Page: 2612
Publisher DOI: 10.1016/j.tetasy.2007.10.025
Abstract: A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels-Alder (HDA) reaction, a Suzuki-Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh_{2}(R-BPTPI)_{4}, provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee.
Relation: http://www.sciencedirect.com/science/journal/09574166
Type: article (author version)
URI: http://hdl.handle.net/2115/32289
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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