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

Sarah M. Pound, Steven J. Underwood, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2448-2453
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number16
DOIs
StatePublished - May 3 2020

Bibliographical note

Funding Information:
We thank the NIH for funding this work (R01 GM095559). We thank Prof. Tom Hoye (UMN) for use of an LCMS.

Publisher Copyright:
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Alkaloids
  • Cross coupling
  • Natural products
  • Photoredox

PubMed: MeSH publication types

  • Journal Article

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