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

Hanari, Taiki; Shimada, Naoyuki; Kurosaki, Yasunobu; Thrimurtulu, Neetipalli; Nambu, Hisanori; Anada, Masahiro; Hashimoto, Shunichi

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

Hanari, Taiki; Shimada, Naoyuki; Kurosaki, Yasunobu et al.

Chemistry-A European journal, 2015, 21(33), 11671-11676

Permalink : https://hdl.handle.net/2115/62685

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アクセス権	open access
URI	https://hdl.handle.net/2115/62685
タイトル	Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition
著者	Hanari, Taiki ; Shimada, Naoyuki ; Kurosaki, Yasunobu ; Thrimurtulu, Neetipalli ; Nambu, Hisanori ; Anada, Masahiro ; Hashimoto, Shunichi
著者名 Hanari, Taiki
著者名 Shimada, Naoyuki
著者名 Kurosaki, Yasunobu
著者名 Thrimurtulu, Neetipalli
e-Rad_Researcher 80399956 著者名 Nambu, Hisanori
e-Rad_Researcher 90344473 著者名 Anada, Masahiro
e-Rad_Researcher 80107391 著者名 Hashimoto, Shunichi
言語	英語
キーワード	(-)-englerin A
	1,3-dipolar cycloaddition
	asymmetric synthesis
	carbonyl ylide
	dirhodium(II) complexes
	total synthesis
発行日	2015-08-10
出版者	Wiley-Blackwell
収録物名	Chemistry-A European journal
巻(号)	21(33)
ページ	11671-11676
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	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
PISSN	0947-6539
関連情報	PMID 26179743
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1002/chem.201502009