What question did this study set out to answer?

The research aims to achieve the stereocontrolled total synthesis of (+)-penicibilaenes A and B.

January 22, 2026Organic Letters1 citations

Total Syntheses of (+)-Penicibilaenes A and B via Enantioselective Desymmetrization

TITaiga IwanagaNagasaki University SKSatoshi KishimotoNagasaki University HFHayato FukudaUniversity of Nagasaki

Key Points

The research aims to achieve the stereocontrolled total synthesis of (+)-penicibilaenes A and B.
Utilized Pd-catalyzed enantioselective desymmetrization to create chiral intermediates.
Employed ring-closing metathesis to construct the bicyclo[3.3.1]nonane core.
Applied intramolecular nitrile oxide [3 + 2] cycloaddition for assembling the dodecane skeleton.
Successfully synthesized (+)-penicibilaenes A and B through the outlined steps.
Achieved a highly functionalized cyclohexene as a crucial intermediate.
Enabled creation of complex molecular structures with significant stereochemistry.

Abstract

Stereocontrolled total syntheses of (+)-penicibilaenes A and B were accomplished through three key steps: (1) Pd-catalyzed enantioselective desymmetrization to afford a pivotal chiral intermediate having an all-carbon quaternary stereogenic center, (2) ring-closing metathesis to form the bicyclo3.3.1nonane core, and (3) intramolecular nitrile oxide 3 + 2 cycloaddition to assemble the tricyclo6.3.1.01,5dodecane skeleton. Enantioselective desymmetrization delivered a highly functionalized cyclohexene, which provided access to (+)-penicibilaenes A and B.

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