Abstract

The enantiocontrolled preparation of the trans-fused ABC ring system of norzoanthamine is described. The synthesis strategy has incorporated studies of Ireland–Claisen rearrangements of esters derived from 3,3-dimethylacrylic acid. Stereocontrol results from competing chair- and boat-like transition states. Introduction of a nitroalkene by application of a modified Henry reaction facilitates an intramolecular Diels–Alder cycloaddition for an effective and simple transformation to the desired conjugated decalone. A fully functionalized AB ring system leads to the cyclization of the trans-fused cyclohexenone to complete the ABC system via ring-closing metathesis.

Full Text
Published version (Free)

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call