The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)2-NaBH(OAc)3. After the reductive coupling, the derived trione was subjected to intramolecular condensation to construct a madindoline skeleton. (C) 2000 Elsevier Science Ltd.
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