Concise Synthesis of Thapsigargin from Nortrilobolide

François Crestey; Maddalena Toma; Søren Brøgger Christensen

doi:10.1016/j.tetlet.2015.09.024

Concise Synthesis of Thapsigargin from Nortrilobolide

François Crestey, Maddalena Toma, Søren Brøgger Christensen

9 Citations (Scopus)

Abstract

Herein, we describe 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 protocol involves three key steps: the one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, subsequent stereoselective α′-acyloxylation in the presence of Mn(OAc)₃, and a highly stereoselective ketone reduction.

Original language	English
Journal	Tetrahedron Letters
Volume	56
Issue number	43
Pages (from-to)	5896-5898
Number of pages	3
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.024
Publication status	Published - 21 Oct 2015

Keywords

Faculty of Health and Medical Sciences
Thapsigargin
Nortrilobolide
Semissynthesis

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10.1016/j.tetlet.2015.09.024

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title = "Concise Synthesis of Thapsigargin from Nortrilobolide",

abstract = "Herein, we describe 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 protocol involves three key steps: the one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, subsequent stereoselective α′-acyloxylation in the presence of Mn(OAc)3, and a highly stereoselective ketone reduction.",

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",

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doi = "10.1016/j.tetlet.2015.09.024",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Concise Synthesis of Thapsigargin from Nortrilobolide

AU - Crestey, François

AU - Toma, Maddalena

AU - Christensen, Søren Brøgger

PY - 2015/10/21

Y1 - 2015/10/21

N2 - Herein, we describe 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 protocol involves three key steps: the one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, subsequent stereoselective α′-acyloxylation in the presence of Mn(OAc)3, and a highly stereoselective ketone reduction.

AB - Herein, we describe 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 protocol involves three key steps: the one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, subsequent stereoselective α′-acyloxylation in the presence of Mn(OAc)3, and a highly stereoselective ketone reduction.

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

SN - 0040-4039

VL - 56

SP - 5896

EP - 5898

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Concise Synthesis of Thapsigargin from Nortrilobolide

Abstract

Keywords

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