Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

We
report the first total synthesis of the limonoid andirolide
N using a 12-step sequence from commercially available materials.
The final step of this route demonstrates the chemical feasibility
of our biosynthetic proposal that andirolide N arises from 8α-hydroxycarapin.
The strategic use of a degraded limonoid as a platform for the synthesis
of more structurally complex congeners may be a general approach to
obtain limonoids with diverse functional properties.