Racemic synthesis of an intermediate for the formal synthesis of madindoline A and B

ABSTRACT

On the basis of the application of the Darzens/ring-expansion process of cyclobutenedione developed previously by our group, a new strategy for the multisubstituted cyclopentene units of madindoline A and madindoline B has been reported in this paper. In light of the strategy, the synthesis of racemic Omura’s intermediate was finished in four steps and 34% overall yield, which furnished a new formal synthetic route to madindolines A and B.

GRAPHICAL ABSTRACT

KEYWORDS:

• Formal synthesis
• natural products
• ring expansion