Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction

Ruben L.H. Andringa; Nittert Marinus; Daan V. Bunt; Elizabeth R. Haiderer; Robert B. Abramovitch; Christopher D. Brown; Kyu Y. Rhee; Martin D. Witte; Adriaan J. Minnaard

doi:10.1039/d4sc01745e

Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction

Ruben L.H. Andringa
, Nittert Marinus
, Daan V. Bunt
, Elizabeth R. Haiderer
, Robert B. Abramovitch
, Christopher D. Brown
, Kyu Y. Rhee
, Martin D. Witte^*
, Adriaan J. Minnaard^*

^*Corresponding author for this work

Chemical Biology 2

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

2 Citations (Scopus)

166 Downloads (Pure)

Abstract

Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium.

Original language	English
Article number	d4sc01745e
Pages (from-to)	10541-10546
Number of pages	6
Journal	Chemical Science
Volume	15
Issue number	27
Early online date	7-Jun-2024
DOIs	https://doi.org/10.1039/d4sc01745e
Publication status	Published - 21-Jul-2024

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@article{675dec927d034ef6b942a40c9b2fb379,

title = "Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction",

abstract = "Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium.",

author = "Andringa, \{Ruben L.H.\} and Nittert Marinus and Bunt, \{Daan V.\} and Haiderer, \{Elizabeth R.\} and Abramovitch, \{Robert B.\} and Brown, \{Christopher D.\} and Rhee, \{Kyu Y.\} and Witte, \{Martin D.\} and Minnaard, \{Adriaan J.\}",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

year = "2024",

month = jul,

day = "21",

doi = "10.1039/d4sc01745e",

language = "English",

volume = "15",

pages = "10541--10546",

journal = "Chemical Science",

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T1 - Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction

AU - Andringa, Ruben L.H.

AU - Marinus, Nittert

AU - Bunt, Daan V.

AU - Haiderer, Elizabeth R.

AU - Abramovitch, Robert B.

AU - Brown, Christopher D.

AU - Rhee, Kyu Y.

AU - Witte, Martin D.

AU - Minnaard, Adriaan J.

PY - 2024/7/21

Y1 - 2024/7/21

N2 - Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium.

AB - Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium.

UR - https://www.scopus.com/pages/publications/85195827391

U2 - 10.1039/d4sc01745e

DO - 10.1039/d4sc01745e

M3 - Article

AN - SCOPUS:85195827391

SN - 2041-6520

VL - 15

SP - 10541

EP - 10546

JO - Chemical Science

JF - Chemical Science

IS - 27

M1 - d4sc01745e

ER -

Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction

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