|
|
Hokkaido University Collection of Scholarly and Academic Papers >
Faculty of Pharmaceutical Sciences >
Peer-reviewed Journal Articles, etc >
Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition
| Title: | Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition |
| Authors: | Hanari, Taiki Browse this author | | Shimada, Naoyuki Browse this author | | Kurosaki, Yasunobu Browse this author | | Thrimurtulu, Neetipalli Browse this author | | Nambu, Hisanori Browse this author →KAKEN DB | | Anada, Masahiro Browse this author →KAKEN DB | | Hashimoto, Shunichi Browse this author →KAKEN DB |
| Keywords: | (-)-englerin A | | 1,3-dipolar cycloaddition | | asymmetric synthesis | | carbonyl ylide | | dirhodium(II) complexes | | total synthesis |
| Issue Date: | 10-Aug-2015 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Chemistry-A European journal |
| Volume: | 21 |
| Issue: | 33 |
| Start Page: | 11671 |
| End Page: | 11676 |
| Publisher DOI: | 10.1002/chem.201502009 |
| PMID: | 26179743 |
| Abstract: | An asymmetric total synthesis of the guaiane sesquiterpene (-)-englerin A, a potent and selective inhibitor of the growth of renal cancer cell lines, was accomplished. The basis of the approach is a highly diastereo- and enantioselective carbonyl ylide cycloaddition with an ethyl vinyl ether dipolarophile under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], [Rh-2(S-TCPTTL)(4)], to construct the oxabicyclo[3.2.1]octane framework with concomitant introduction of the oxygen substituent at C9 on the exo-face. Another notable feature of the synthesis is ruthenium tetraoxide-catalyzed chemoselective oxidative conversion of C9 ethyl ether to C9 acetate. |
| Rights: | This is the accepted version of the following article: Hanari, T., Shimada, N., Kurosaki, Y., Thrimurtulu, N., Nambu, H., Anada, M. and Hashimoto, S. (2015), Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition. Chem. Eur. J., 21: 11671-11676, which has been published in final form at http://dx.doi.org/10.1002/chem.201502009 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/62685 |
| 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
|
