The first total synthesis of the paracaseolide A, a very unusual tetraquinane oxa-cage bislactone recently isolated from the mangrove Sonneratia paracaseolaris, has been achieved. The final step and culmination of the eight-step synthetic sequence is a [4 + 2] dimerization of a 4-hydroxybutenolide, generated by singlet oxygen-mediated oxidation of a furan precursor.
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Waseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan
Mukaeda, Yuki
Kawahara, Ryo
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Waseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan
Kawahara, Ryo
Tatsuta, Kuniaki
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Waseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan