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

doi:10.1002/ejoc.202000158

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

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3 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 language	English (US)
Pages (from-to)	2448-2453
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.202000158
State	Published - May 3 2020
Externally published	Yes

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

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10.1002/ejoc.202000158

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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.",

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AU - Pound, Sarah M.

AU - Underwood, Steven J.

AU - Douglas, Christopher J.

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AB - 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.

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KW - Photoredox

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

Abstract

Bibliographical note

Keywords

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