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Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition

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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

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