Concise Synthesis of Thapsigargin from Nortrilobolide
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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
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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