Asymmetric Total Synthesis of (−)‐Englerin A through Catalytic Diastereo‐ and Enantioselective Carbonyl Ylide Cycloaddition. Issue 33 (15th July 2015)

• Record Type: Journal Article
• Authors: Hanari, Taiki; Shimada, Naoyuki; Kurosaki, Yasunobu; Thrimurtulu, Neetipalli; Nambu, Hisanori; Anada, Masahiro; Hashimoto, Shunichi
• Is Part Of: Chemistry. Volume 21:Issue 33(2015)
• Page Start: 11671
• Page End: 11676
• Publication Date: 2015-07-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201502009
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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[<italic>N</italic>‐tetrachlorophthaloyl‐(<italic>S</italic>)‐<italic>tert</italic>‐leucinate], [Rh₂(<italic>S</italic>‐TCPTTL)₄], to construct the oxabicyclo[3.2.1]octane framework with concomitant introduction of the oxygen substituent at C9 on the <italic>exo</italic>‐face. Another notable feature of the synthesis is ruthenium tetraoxide‐catalyzed chemoselective oxidative conversion of C9 ethyl ether to C9 acetate.</p> </abstract>