cas 20267-87-2, CHELIDONINE MONOHYDRATE* | Articles data ｜lookchem

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20267-87-2

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A NOVEL AND BIOMIMETIC SYNTHESIS OF (+/-)-CHELAMINE, (+/-)-CHELIDONINE, SANGUINARINE, AND DIHYDROSANGUINARINE FROM COPTISINE VIA A COMMON INTERMEDIATE
(+/-)-Chelamine and (+/-)-chelidonine, B/C cis hexahydrobenzophenanthridine alkaloids were stereoselectively synthesized from coptisine via the key intermediate, which was also converted to fully aromatized benzophenanthridine alkaloids, sanguinarine and dihydrosanguinarine.
Hanaoka, Miyoji,Yoshida, Shuji,Annen, Masami,Mukai, Chisato
p. 739 - 742
(1986)
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Total Synthesis of (+/-)-Chelidonine
Condensation of the Schiff base 8 with 3,4-(methylenedioxy)homophthalic anhydride (13) was exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (+/-)-chelidonine (1).A variety of reaction conditions were investigated in order to maximize the production of the desired thermodynamically less stable cis diastereomer.A method was devised for the conversion of 24 to its acid chloride without production of the indenoisoquinoline 30.The migration of an aromatic ring was observed on treatment of the diazo ketone 26 with acid.This reaction is reminiscent of the Hayashi rearrangement.
Cushman, Mark,Choong, Tung-Chung,Valko, Joseph T.,Koleck, Mary P.
p. 5067 - 5073
(1980)
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Oppolzer,W.,Keller,K.
p. 3836 - 3837
(1971)
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A TOTAL SYNTHESIS OF CHELIDONINE
Condensation of homophthalic anhydride 3 with the Schiff base 4 is exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (+/-)-chelidone (8).
Cushman, Mark,Choong, T.-C.,Valko, Joseph T.,Koleck, Mary P.
p. 3845 - 3848
(1980)
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Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2+2] cycloaddition cascade
Total syntheses of chelidonine and norchelidonine featuring an enamide-benzyne-[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels-Alder reaction.
Ma, Zhi-Xiong,Feltenberger, John B.,Hsung, Richard P.
p. 2742 - 2745
(2012/08/07)

Highly stereoselective total syntheses of (±)-chelidonine and of (±)-norchelidonine by an intramolecular o-quinodimethane/nitrostyrene-cycloaddition
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Oppolzer,Robbiani
p. 1119 - 1128
(2007/10/02)

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Chemical Properties

Melting Point: 135-136oC(lit.)
Boiling Point: 507.4±50.0 °C(Predicted)
Density: 1.422±0.06 g/cm3(Predicted)
Storage Temp.:2-8°C
PKA: 14.11±0.20(Predicted)
Merck: 13,2061
PSA: 69.62000
LogP: 2.20490

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