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Total synthesis of zaragozic acid C by an aldol-based strategy
| Title: | Total synthesis of zaragozic acid C by an aldol-based strategy |
| Authors: | Nakamura, Seiichi1 Browse this author | | Sato, Hiroki2 Browse this author | | Hirata, Yuuki3 Browse this author | | Watanabe, Nobuhide4 Browse this author | | Hashimoto, Shunichi5 Browse this author →KAKEN DB |
| Authors(alt): | 中村, 精一1 | | 佐藤, 浩樹2 | | 平田, 勇樹3 | | 渡邉, 信英4 | | 橋本, 俊一5 |
| Keywords: | Zaragozic acids | | Aldol reaction | | α-Keto ester | | Silyl ketene thioacetal | | Internal ketalization |
| Issue Date: | 21-Nov-2005 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron |
| Volume: | 61 |
| Issue: | 47 |
| Start Page: | 11078 |
| End Page: | 11106 |
| Publisher DOI: | 10.1016/j.tet.2005.09.030 |
| Abstract: | A total synthesis of zaragozic acid C by a convergent strategy is described in which the key features include (1) the simultaneous creation of the C4 and C5 quaternary stereogenic centers by a Sn(OTf)2-promoted aldol coupling reaction between an α-keto ester and a silyl ketene thioacetal derived from L- and D-tartaric acids, respectively, (2) the direct introduction of lithium acetylide as the C1 side chain equivalent onto the fully functionalized aldehyde, and (3) construction of the bicyclic core structure by acid-catalyzed internal ketalization under kinetically controlled conditions. |
| Relation: | http://www.sciencedirect.com/science/journal/00404020 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/727 |
| 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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