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Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L
| 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)
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Submitter: 穴田 仁洋
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