Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments

The drimentine family is a class of hybrid isoprenoids derived from actinomycete bacteria. Members of this family display weak antitumor and antibacterial activity. Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium‐catalyzed cyanoamidation, reductive cross‐coupling, and photoredox‐catalyzed α‐alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l ‐tryptophan, l ‐proline, and (+)‐sclareolide.