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Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments
Author(s) -
Pound Sarah M.,
Underwood Steven J.,
Douglas Christopher J.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000158
Subject(s) - chemistry , total synthesis , terpenoid , alkylation , aldehyde , stereochemistry , convergent synthesis , palladium , reductive amination , combinatorial chemistry , catalysis , organic chemistry
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.