Synthesis of (+)-Madindoline A and (+)-Madindoline B
journal contributionposted 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.