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Stereoselective synthesis of a C1-C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence
| Title: | Stereoselective synthesis of a C1-C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence |
| Authors: | Nakamura, Seiichi1 Browse this author | | Kikuchi, Fumiaki2 Browse this author | | Hashimoto, Shunichi3 Browse this author →KAKEN DB |
| Authors(alt): | 中村, 精一1 | | 菊地, 史朗2 | | 橋本, 俊一3 |
| Issue Date: | 16-May-2008 |
| Publisher: | Pergamon |
| Journal Title: | Tetrahedron Asymmetry |
| Volume: | 19 |
| Issue: | 9 |
| Start Page: | 1059 |
| End Page: | 1067 |
| Publisher DOI: | 10.1016/j.tetasy.2008.04.013 |
| Abstract: | A C1–C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a γ,δ-trans-dimethylsubstituted α-methylene lactone, has been synthesized in an optically pure form from ethyl (E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction would be a result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone. |
| Relation: | http://www.sciencedirect.com/science/journal/09574166 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/33049 |
| 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: 中村 精一
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