Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments. Issue 16 (17th April 2020)

• Record Type: Journal Article
• Authors: Pound, Sarah M.; Underwood, Steven J.; Douglas, Christopher J.
• Other Names: Aggarwal Varinder K. guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 16(2020)
• Page Start: 2448
• Page End: 2453
• Publication Date: 2020-04-17
• Subjects: Natural products -- Alkaloids -- Photoredox -- Cross coupling; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000158
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : Synthetic efforts towards the total synthesis of the natural product drimentine C are described. Three distinct approaches are discussed incorporating palladium‐catalyzed cyanoamidation, reductive cross‐coupling and photoredox‐catalyzed α‐alkylation of an aldehyde as key steps to join the alkaloid and terpenoid fragments.