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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

2 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

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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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.

N1 - 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

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N2 - 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.

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 - Cross coupling

KW - Natural products

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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