%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