cas 67526-95-8, (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate

Articles about 67526-95-8Total 6 be found

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METHOD FOR PREPARATION OF INTERMEDIATES USEFUL FOR PREPARATION OF THAPSIGARGIN AND NORTRILOBOLIDE
The present invention relates to the preparation of Thapsigargin (1) and Nortrilobolide (2). The invention further relates to intermediates and preparation of said intermediates which are useful for the preparation of (1) and (2).
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(2018/09/25)

SYNTHESIS OF THAPSIGARGIN, NORTRILOBOLIDE, AND ANALOGS THEREOF
The present invention relates to the preparation of compounds of Formula I, including thapsigargin, nortrilobolide and 8-O-debutanoyl-thapsigargin from commercially available (R)-(-)-carvone via synthetic intermediate compound of formula 12 by pinacol coupling and in situ lactonization.
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(2018/10/25)

A Concise, Efficient and Scalable Total Synthesis of Thapsigargin and Nortrilobolide from (R)-(?)-Carvone
A concise, efficient and scalable synthesis of thapsigargin and nortrilobolide from commercially available (R)-(?)-carvone was developed. Our synthetic strategy is inspired by nature’s carbon-carbon bond formation sequence, which facilitates the construction of a highly functionalized sesquiterpene lactone skeleton in five steps via an enantioselective ketone alkylation and a diastereoselective pinacol cyclization. We envision that this strategy will permit the construction of other members of the family, structural analogs and provide a practical synthetic route to these important bioactive agents. In addition, we anticipate that the prodrug Mipsagargin, which is currently in late-stage clinical trials for the treatment of cancer, will also be accessible via this strategy. Hence, the limited availability from natural sources, coupled with an estimated demand of one metric ton per annum for the prodrug, provides a compelling mandate to develop practical total syntheses of these agents.
Chen, Dezhi,Evans, P. Andrew
p. 6046 - 6049
(2017/05/09)

Concise synthesis of thapsigargin from nortrilobolide
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.
Crestey, Fran?ois,Toma, Maddalena,Christensen, S?ren Br?gger
p. 5896 - 5898
(2015/11/02)

Total synthesis of thapsigargin, a potent SERCA pump inhibitor
The enantioselective total synthesis of thapsigargin, a potent, selective inhibitor of the Ca2+ pump SERCA, is described. Starting from ketoalcohol 8, key steps involve regioselective introduction of the internal olefin at C4-C5, judicious protecting group choice to allow chelation-controlled reduction at C3, and chemoselective introduction of the angelate ester function at C3-0. A selective esterification approach completes the total synthesis in a total of 42 steps and 0.61% overall yield (88.6% average yield per step).
Ball, Matthew,Andrews, Stephen P.,Wierschem, Frank,Cleator, Ed,Smith, Martin D.,Ley, Steven V.
p. 663 - 666
(2008/02/05)

Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition
Herein we describe the total synthesis of five guaianolide natural products: thapsigargin. thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.
Andrews, Stephen P.,Ball, Matthew,Wierschem, Frank,Cleator, Ed,Oliver, Steven,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Huenger, Udo,Smith, Martin D.,Ley, Steven V.
p. 5688 - 5712
(2008/02/13)

Chemical Properties

Appearance/Colour :colourless film
Boiling Point: 691.9 °C at 760 mmHg
Flash Point:206.1 °C
Density: 1.23 g/cm³
Solubility:DMSO: soluble
Storage Temp.:-20°C
Vapor Pressure: 3.78E-22mmHg at 25°C
Refractive Index: 1.539
PKA: 10.57±0.70(Predicted)
PSA: 171.96000
LogP: 3.92790

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Chemical Properties

Appearance/Colour :colourless film

Boiling Point: 691.9 °C at 760 mmHg

Flash Point:206.1 °C

Density: 1.23 g/cm³

Solubility:DMSO: soluble

Storage Temp.:-20°C

Vapor Pressure: 3.78E-22mmHg at 25°C

Refractive Index: 1.539

PKA: 10.57±0.70(Predicted)

PSA: 171.96000

LogP: 3.92790

Global suppliers and manufacturers of 67526-95-8total 49 suppliers on LookChem

Article Database

67526-95-8

Articles about 67526-95-8Total 6 be found

More Articles about upstream products of 67526-95-8

Chemical Properties

Appearance/Colour :colourless film

Boiling Point: 691.9 °C at 760 mmHg

Flash Point:206.1 °C

Density: 1.23 g/cm3

Solubility:DMSO: soluble

Storage Temp.:-20°C

Vapor Pressure: 3.78E-22mmHg at 25°C

Refractive Index: 1.539

PKA: 10.57±0.70(Predicted)

PSA: 171.96000

LogP: 3.92790

Global suppliers and manufacturers of 67526-95-8total 49 suppliers on LookChem

Density: 1.23 g/cm³