Concise Synthesis of Thapsigargin from Nortrilobolide

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Standard

Concise Synthesis of Thapsigargin from Nortrilobolide. / Crestey, François; Toma, Maddalena; Christensen, Søren Brøgger.

I: Tetrahedron Letters, Bind 56, Nr. 43, 08.09.2015, s. 5896-5898.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Crestey, F, Toma, M & Christensen, SB 2015, 'Concise Synthesis of Thapsigargin from Nortrilobolide', Tetrahedron Letters, bind 56, nr. 43, s. 5896-5898. https://doi.org/10.1016/j.tetlet.2015.09.024

APA

Crestey, F., Toma, M., & Christensen, S. B. (2015). Concise Synthesis of Thapsigargin from Nortrilobolide. Tetrahedron Letters, 56(43), 5896-5898. https://doi.org/10.1016/j.tetlet.2015.09.024

Vancouver

Crestey F, Toma M, Christensen SB. Concise Synthesis of Thapsigargin from Nortrilobolide. Tetrahedron Letters. 2015 sep. 8;56(43):5896-5898. https://doi.org/10.1016/j.tetlet.2015.09.024

Author

Crestey, François ; Toma, Maddalena ; Christensen, Søren Brøgger. / Concise Synthesis of Thapsigargin from Nortrilobolide. I: Tetrahedron Letters. 2015 ; Bind 56, Nr. 43. s. 5896-5898.

Bibtex

@article{b0af404e81cd478aa65d3c6e28750221,
title = "Concise Synthesis of Thapsigargin from Nortrilobolide",
abstract = "Herein, we wish to describe for the first time an expedient synthesis of the hexaoxygenated guaianolide thapsigargin (1), a potent inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), from the natural product nortrilobolide (2). This innovative protocol involves three key steps: a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, a stereoselective α´-acyloxylation in the presence of Mn(OAc)3 and a highly stereoselective reduction of a ketone into its corresponding alcohol highlighting the vital importance of the solvent used during the reaction.",
keywords = "Faculty of Health and Medical Sciences, Thapsigargin, Nortrilobolide, Semissynthesis",
author = "Fran{\c c}ois Crestey and Maddalena Toma and Christensen, {S{\o}ren Br{\o}gger}",
year = "2015",
month = sep,
day = "8",
doi = "10.1016/j.tetlet.2015.09.024",
language = "English",
volume = "56",
pages = "5896--5898",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Pergamon Press",
number = "43",

}

RIS

TY - JOUR

T1 - Concise Synthesis of Thapsigargin from Nortrilobolide

AU - Crestey, François

AU - Toma, Maddalena

AU - Christensen, Søren Brøgger

PY - 2015/9/8

Y1 - 2015/9/8

N2 - Herein, we wish to describe for the first time an expedient synthesis of the hexaoxygenated guaianolide thapsigargin (1), a potent inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), from the natural product nortrilobolide (2). This innovative protocol involves three key steps: a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, a stereoselective α´-acyloxylation in the presence of Mn(OAc)3 and a highly stereoselective reduction of a ketone into its corresponding alcohol highlighting the vital importance of the solvent used during the reaction.

AB - Herein, we wish to describe for the first time an expedient synthesis of the hexaoxygenated guaianolide thapsigargin (1), a potent inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), from the natural product nortrilobolide (2). This innovative protocol involves three key steps: a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, a stereoselective α´-acyloxylation in the presence of Mn(OAc)3 and a highly stereoselective reduction of a ketone into its corresponding alcohol highlighting the vital importance of the solvent used during the reaction.

KW - Faculty of Health and Medical Sciences

KW - Thapsigargin

KW - Nortrilobolide

KW - Semissynthesis

U2 - 10.1016/j.tetlet.2015.09.024

DO - 10.1016/j.tetlet.2015.09.024

M3 - Journal article

VL - 56

SP - 5896

EP - 5898

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 43

ER -

ID: 143966668