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Synthesis of (+)-Madindoline A and (+)-Madindoline B

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journal contribution
posted on 15.02.2007, 00:00 by Lifeng Wan, Marcus A. Tius
The allene ether version of the Nazarov cyclization was used to construct the cyclopentane dione portion of madindolines A and B. The racemic cyclopentane dione from the Nazarov cyclization was converted to an enol ether that was combined with the chiral, nonracemic hydroxyfuroindoline in a Mannich reaction. Deprotection and oxidation led to (+)-madindoline A and (+)-madindoline B.