Journal Article 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

21 ( 33 )  , pp.11671 - 11676 , 2015-08-10 , Wiley-Blackwell
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.

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