%0 Journal Article %A Akai, Shuji %A Tsujino, Toshiaki %A Fukuda, Nobuhisa %A Iio, Kiyosei %A Takeda, Yoshifumi %A Kawaguchi, Ken-ichi %A Naka, Tadaatsu %A Higuchi, Kazuhiro %A Kita, Yasuyuki %D 2001 %T Enantiodivergent Synthesis of Either Enantiomer of ABCDE-Ring Analogue of Antitumor Antibiotic Fredericamycin A via Intramolecular [4 + 2] Cycloaddition Approach %U https://acs.figshare.com/articles/journal_contribution/Enantiodivergent_Synthesis_of_Either_Enantiomer_of_ABCDE-Ring_Analogue_of_Antitumor_Antibiotic_Fredericamycin_A_via_Intramolecular_4_2_Cycloaddition_Approach/3740484 %R 10.1021/ol016696y.s001 %2 https://acs.figshare.com/ndownloader/files/5832252 %K fredericamycin %K Enantiomer %K analogue %K Approach %K Key steps %K cycloaddition %K Antitumor Antibiotic Fredericamycin %K enantiomer %K intramolecular enantiodivergent synthesis %K ethoxyvinyl %K enantioselective %K Enantiodivergent Synthesis %K furoate %K desymmetrization %K Intramolecular %K prochiral diol 2 %K Analogue %K Cycloaddition %X An intramolecular enantiodivergent synthesis of both enantiomers of the ABCDE-ring analogue 22 of fredericamycin A is reported. Key steps involve an intramolecular [4 + 2] cycloaddition of 17 and an aromatic Pummerer-type reaction of 19. A lipase-catalyzed enantioselective desymmetrization of prochiral diol 2 using 1-ethoxyvinyl 2-furoate 3 led to the pivotal intermediate (R)-4. %I ACS Publications