Wharton-Fragmentation-Based Approach to the Carbocyclic Core of the Phomoidrides

The carbocyclic core of the phomoidrides has been synthesized efficiently and in high yield. Key steps include a phenolic oxidation/intramolecular Diels–Alder sequence, tandem radical cyclization, and a late-stage Wharton fragmentation of a densely functionalized isotwistane skeleton

Toward the Synthesis of Phomoidride D

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels–Alder cycloaddition and a tandem 5-<i>exo</i>-<i>trig</i>/5-<i>exo</i>-<i>trig</i> radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]­decene

Toward the Synthesis of Phomoidride D

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels–Alder cycloaddition and a tandem 5-<i>exo</i>-<i>trig</i>/5-<i>exo</i>-<i>trig</i> radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]­decene