Unified Biomimetic Approach to (+)-Hippolachnin A: In-Depth Insights into Its Biosynthetic Origin

A formal biomimetic synthesis of (+)-hippolachnin A has been achieved under the guidance of its plausible biosynthetic pathway. Pivotal transformations include an intriguing O-1(2)-mediated [4 + 2] cycloaddition and a tandem Kornblum-DeLaMare rearrangement/hemiketalization/dehydration reaction. The current work not only offers a unified approach to access skeletally diverse plakortin-type polyketides but also provides convincing evidence to elucidate their underlying biosynthetic network.

Automated summary

This study successfully achieved the formal biomimetic synthesis of (+)-hippolachnin A guided by its plausible biosynthetic pathway. Key transformations include an intriguing [4 + 2] cycloaddition and a tandem rearrangement/dehydration reaction. The work not only provides a unified approach to access diverse plakortin-type polyketides but also offers convincing evidence to elucidate their underlying biosynthetic network.