4984-99-0

Usage

InChI:InChI=1/C19H19NO4/c1-20-4-3-19-9-18(22-2)15(21)7-13(19)14(20)5-11-6-16-17(8-12(11)19)24-10-23-16/h6-9,14H,3-5,10H2,1-2H3/t14-,19+/m1/s1

Upstream product

• 4850-04-8 Nudaurin 
• 42971-24-4 6,7-dimethoxy-1-(3',4'-methylenedioxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 27675-60-1 1-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol 
• 169304-62-5 (1R,4aR,2'S)-1,2,3,4,4a,7-hexahydro-7-oxo-4a-(2'-phenylpropionyloxy)-2-trifluoroacetyl-1-piperonylisoquinoline 
• 169304-64-7 (9R)-(-)-N-trifluoroacetylnoramurine 
• 71046-75-8 1,2,3,4-tetrahydro-6-methoxy-1-(3',4'-methylenedioxy)benzyl-N-trifluoroacetylisoquinolin-7-ol 
• 50-00-0 formaldehyd 
• 171595-33-8 (9R)-(+)-noramurine 

Downstream Products

• 19452-63-2 5,6α,8,14β-Tetrahydro-amurin 
• 4850-04-8 Nudaurin 
• 402469-62-9 2,3-methanediyldioxy-6-methoxy-17-methyl-morphina-5,8(14)-dien-7α-ol 

Relevant academic research and scientific papers

The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid

The non-phenolic coupling reaction of benzyltetrahydroisoquinolines (laudanosine derivatives) by using a hypervalent iodine(III) reagent is described. In general, chemical oxidation of laudanosine gives glaucine. In contrast to general chemical oxidizing reagent systems, the novel use of reagent combination of phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) afforded morphinandienone alkaloids in excellent yields. In order to achieve the coupling reaction with simple reaction procedure, the use of HPA supported on silica gel instead of HPA was demonstrated and sufficient yield was exerted again. The present reagent system, PIFA/HPA, was also applied to the oxidation of other non-phenolic benzyltetrahydroisoquinolines and the high yield conversion to morphinandienones was accomplished.

Synthesis of optically active aporphine and morphinandienone alkaloids via p-quinol esters

Lead tetraacetate oxidation of N-trifluoroacetylnorcodamine (5) in (S)-(+)-2-phenylpropionic acid gave a diastereomeric mixture of two p-quinol acylates, which were easily separated to enantiomerically pure 6a and 6b. Treatment of the chiral quinol acylates (6a) and (6b) with trifluoroacetic acid in CH2Cl2 at room temperature afforded (1R)-(-)-6-trifluoroacetylwilsonirine (7a) and (1S)-(+)-(7b), respectively. Saponification of 7a and 7b gave rise to (-)-wilsonirine (8a) and its enantiomer (8b), respectively. Similarly, (-)-nordomesticine (12a) and (+)-(12b) were synthesized in enantiomerically pure form from 10a and 10b. On the other hand, acid treatment of 6a and 6b in CH3CN at lower temperature (-30°C) llowed by N-deprotection gave the corresponding normorphinandienones (15a and 15b) as major products, which were transformed to enantiomerically pure (-)-16a and (+)-sebiferine (16b). In a similar sequence of reactions, (+)-amurine (19a) and its enantiomer (19b) were synthesized.

ALKALOIDS OF Papaver nudicaule SUBSP. xanthopetalum (TRAUTV.) FEDDE AND P. nudicaule SUBSP. album (REGEL) FEDDE FROM THE SECTION Scapiflora REICHB.

The alkaloidal composition in the two taxa differs only quantitatively.Both contain amurine as the main alkaloid.P. nudicaule ssp. xanthopetalum contains muramine, protopine and alkaloid PN1 (probably identical with (+/-)-nudaurine (Ia)) as dominant alkaloids; further were isolated amurensine, epialpinine, cryptopine, mecambridine and alpinigenine.Allocryptopine, papaverrubines A, B, D and G, palmatine and coptisine were detected chromatographically.The quaternary alkaloid fraction afforded cis-N-methylstylopinium hydroxide (as the iodide II) which was isolated for the first time from P. nudicaule.In P. nudicaule ssp. album the alkaloid PN1, epialpinine, amurensine and muramine represented the dominant alkaloids, accompanied with mecambridine, protopine, cryptopine, allocryptopine and alpinigenine.Among the quaternary alkaloids N-methylstylopinium hydroxide was found.