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Catalytic asymmetric synthesis of descurainin via 1,3-dipolar cycloaddition of a carbonyl ylide using Rh2(R-TCPTTL)4
| Title: | Catalytic asymmetric synthesis of descurainin via 1,3-dipolar cycloaddition of a carbonyl ylide using Rh2(R-TCPTTL)4 |
| Authors: | Shimada, Naoyuki Browse this author | | Hanari, Taiki Browse this author | | Kurosaki, Yasunobu Browse this author | | Anada, Masahiro Browse this author | | Nambu, Hisanori Browse this author | | Hashimoto, Shunichi Browse this author |
| Keywords: | Carbonyl ylide | | 1,3-Dipolar cycloaddition | | Chiral dirhodium(II) catalyst | | Descurainin |
| Issue Date: | 15-Dec-2010 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron Letters |
| Volume: | 51 |
| Issue: | 50 |
| Start Page: | 6572 |
| End Page: | 6575 |
| Publisher DOI: | 10.1016/j.tetlet.2010.10.036 |
| Abstract: | A catalytic asymmetric synthesis of descurainin has been achieved by incorporating an enantioselective 1,3-dipolar cycloaddition, a stereoselective alkene hydrogenation, an oxidation with Fremy's salt and a regioselective demethylation with NbCl5 as the key steps. The 1,3-dipolar cycloaddition of a carbonyl ylide derived from tert-butyl 2-diazo-5-formyl-3-oxopetanoate with 4-hydroxy-3-methoxyphenylacetylene in the presence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinate], Rh2(R-TCPTTL)4, provided an 8-oxabicyclo[3.2.1]octane skeleton in 95% ee. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/44674 |
| 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: 南部 寿則
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