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Synthesis of (+)-madindoline A and (+)-madindoline B.

ABSTRACT: 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. [reaction: see text].

SUBMITTER: Wan L 

PROVIDER: S-EPMC2516479 | biostudies-other | 2007 Feb

REPOSITORIES: biostudies-other

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Synthesis of (+)-madindoline A and (+)-madindoline B.

Wan Lifeng L   Tius Marcus A MA  

Organic letters 20070201 4

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. [reaction: see text]. ...[more]