cas 482-85-9, (-)-ISORESERPINE | Articles data ｜lookchem

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482-85-9

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A Desymmetrization-Based Total Synthesis of Reserpine
Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.
Park, Jisook,Chen, David Y.-K.
p. 16152 - 16156
(2018/11/23)

Regiospecific and stereoselective syntheses of (±)-reserpine and (-)-reserpine
Full details of three approaches to an entirely regio- and Stereoselective synthesis of the well-known target reserpine are described, culminating in a total synthesis which efficiently meets these requirements.
Stork, Gilbert,Tang, Peng Cho,Casey, Michael,Goodman, Burton,Toyota, Masahiro
p. 16255 - 16262
(2007/10/03)

Novel zinc mediated indole ring opening of isoreserpine
Reaction of reserpine'(1) with Zn/TFA resulted in isoreserpine (2), dihydro compound (7), and amino compound (8) via initial epimerization at C- 3. The latter two compounds constitute a novelty in indole alkaloid chemistry: the dihydro compound (7) posses
Berner, Mathias,Tolvanen, Arto,Lounasmaa, Mauri,Jokela, Reija
p. 2941 - 2948
(2007/10/03)

Reinvestigation of the Mechanism of the Acid-Catalyzed Epimerization of Reserpine to Isoreserpine
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Zhang, Lin-Hua,Gupta, Ashok K.,Cook, James M.
p. 4708 - 4712
(2007/10/02)

Genaral Strategies for the Synthesis of Indole Alkaloids. Total Syntheses of (+/-)-Reserpine and (+/-)-α-Yohimbine
The concise, total syntheses of the indole alkaloids (+/-)-reserpine (1) and (+/-)-α-yohimbine (4) have been completed by the application of a general strategy that features an intramolecular Diels-Alder reaction for the facile construction of the functio
Martin, Stephen F.,Rueeger, Heinrich,Williamson, Sidney A.,Grzejszczak, Slawomir
p. 6124 - 6134
(2007/10/02)

Total Synthesis of (+/-)-Reserpine
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Martin, Stephen F.,Grzejszczak, Slawomir,Rueeger, Heinrich,Williamson Sidney A.
p. 4072 - 4074
(2007/10/02)

Studies on the photostability of reserpine in parenteral solutions
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Jamil,Afrozrizvi,Ahmed,Ejazbeg
p. 467 - 469
(2007/10/02)

General Methodology for cis-Hydroisoquinoline Synthesis: Synthesis of Reserpine
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Wender, P. A.,Schaus, J. M.,White, A. W.
p. 6157 - 6159
(2007/10/02)

Photooxidation of reserpine.
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Wright,Tang
p. 299 - 300
(2007/10/04)

On dehydroreserpine.
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KREBS,FUTSCHER
p. 75 - 78
(2007/10/04)

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Chemical Properties

Melting Point: 148-155 °C(lit.)
Boiling Point: 700.1°Cat760mmHg
Flash Point:377.2°C
Density: 1.32g/cm³
PKA: 18.11±0.70(Predicted)
PSA: 117.78000
LogP: 4.10900

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