220751-83-7

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one is used as a potential pharmaceutical agent for its unique structural features and potential biochemical activity. (3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one's high polarity and water solubility, along with its specific stereochemistry, may contribute to its efficacy in targeting specific biological pathways or interacting with certain receptors, making it a candidate for the development of new drugs.
Used in Biological Research:
In the field of biological research, (3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one serves as a valuable compound for studying the effects of stereochemistry on molecular interactions and biological activity. Its complex structure allows researchers to investigate the role of specific functional groups and their arrangement in influencing the compound's properties and potential applications in medicine and biology.

Upstream product

• 40041-97-2 (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one 
• 474526-61-9 (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-1,1a,2,3,4,4a,5,6-octahydrophenanthridine 
• 474526-57-3 (1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol 
• 474526-62-0 11-acetoxy-12-(tert-butyl-dimethyl-silanyloxy)-6-diethylcarbamoyloxy-2,2-dimethyl-5-oxo-3a,5,10b,11,12,12a-hexahydro-3bH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthrene-4-carboxylic acid tert-butyl ester 
• 474526-59-5 (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine 
• 54162-19-5 2,4-Cyclohexadien-1-carbonsaeure-methylester 
• 69393-72-2 2H-benzo[d][1,3]dioxolan-4-ol 
• 82299-36-3 bromo-5 hydroxy-4 benzodioxole-1,3 
• 200182-30-5 methyl 2-hydroxy-7-oxabicyclo[4.1.0]hept-3-ene-4-carboxylate 
• 106861-61-4 (+)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate 
• 71-43-2 benzene 

Downstream Products

• 29477-83-6 (2R,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 
• 40042-02-2 (3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione 

Relevant academic research and scientific papers

Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene

Enantioselective total syntheses of the anticancer isocarbostyril alkaloids (+)-7-deoxypancratistatin, (+)-pancratistatin, (+)-lycoricidine, and (+)-narciclasine are described. Our strategy for accessing this unique class of natural products is based on the development of a Ni-catalyzed dearomative trans-1,2-carboamination of benzene. The effectiveness of this dearomatization approach is notable, as only two additional olefin functionalizations are needed to construct the fully decorated aminocyclitol cores of these alkaloids. Installation of the lactam ring has been achieved through several pathways and a direct interconversion between natural products was established via a late-stage C-7 cupration. Using this synthetic blueprint, we were able to produce natural products on a gram scale and provide tailored analogs with improved activity, solubility, and metabolic stability.

Biological evaluation of ent-narciclasine, ent-lycoricidine, and certain enantiomerically-related congeners

The non-natural enantiomeric forms of narciclasine and lycoricidine ((-)-1 and (-)-2, respectively), as well as congeners 3-6 are available through chemoenzymatic synthesis. Accordingly, they have now been tested for their cytotoxic effects in a 13-member

ISOCARBOSTYRIL ALKALOIDS AND FUNCTIONALIZATION THEREOF

Enantioselective total syntheses of the anticancer isocarbostyril alkaloids (+)-7-deoxypancratistatin, (+)-pancratistatin, (+)-lycoricidine, and (+)-narciclasine are described. Our strategy for accessing this unique class of natural products is based on the development of a Ni-catalyzed dearomative trans-1,2-carboamination of benzene. The effectiveness of this dearomatization approach is notable, as only two additional olefin functionalizations are needed to construct the fully decorated aminocyclitol cores of these alkaloids. Installation of the lactam ring has been achieved through several pathways and a direct interconversion between natural products was established via a late-stage C-7 cupration. Using this synthetic blueprint, we were able to produce natural products on a gram scale and provide tailored analogs with improved activity, solubility, and metabolic stability.

Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2-epi-Narciclasine

An efficient protocol for the isolation of narciclasine from common Amaryllidaceae bulbs, separation from haemanthamine, and the occurrence of a trace alkaloid, 2-epi-narciclasine, are reported. Attempts to convert natural narciclasine to its C-2 epimer by Mitsunobu inversion or oxidation/reduction sequences were compromised by rearrangement and aromatization processes, through which a synthesis of the alkaloid narciprimine was achieved. The methylation of the 7-hydroxy group of natural narciclasine followed by protection of the 3,4-diol function and oxidation/reduction sequence provided the target C-2 epimer. A de novo chemoenzymatic synthesis of 2-epi-narciclasine from m-dibromobenzene is also described. Haemanthamine and narciprimine were readily detected in the crude extracts of Narcissus and Galanthus bulbs containing narciclasine, and the occurrence of 2-epi-narciclasine as a trace natural product in Galanthus sp. is reported for the first time.

Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene

The total synthesis of lycoricidine and narciclasine is enabled by an arenophile-mediated dearomative dihydroxylation of bromobenzene. Subsequent transpositive Suzuki coupling and cycloreversion deliver a key biaryl dihydrodiol intermediate, which is rapidly converted into lycoricidine through site-selective syn-1,4-hydroxyamination and deprotection. The total synthesis of narciclasine is accomplished by the late-stage, amide-directed C?H hydroxylation of a lycoricidine intermediate. Moreover, the general applicability of this strategy to access dihydroxylated biphenyls is demonstrated with several examples.

A chemoenzymatic total synthesis of ent-narciclasine

The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the aminoconduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone

A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling

A facile construction of the typical framework of narcissus alkaloids has been realized by virtue of the development of a practical route involving stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling. To achieve this goal, it proved to be necessary to devise a strategy that would enable chemical transformations to install an epoxy moiety in a congested environment. The successful preparation of a hindered epoxide from O-isopropylidene-protected 4-aminocyclohexenol required three steps consisting principally of controlled bromohydration and base-promoted closure and N-alkylation. It was found that a catalytic amount of SnCl4 not only maintained the catalytic cycle but also effected clean arylation to form a fused BC ring system. Several tactics that ultimately proved to be unsatisfactory are also discussed in an effort to set important boundary limits on arene-epoxide coupling. The requisite enantiopure 4-aminocyclohexenol was available via an asymmetric cycloaddition of diene to camphor-based chloronitroso. The total synthesis of (+)-narciclasine was realized in nine steps with an overall yield of 19%.

Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives.

Biocatalytic approaches have yielded efficient total syntheses of the major Amaryllidaceae alkaloids, all based on the key enzymatic dioxygenation of suitable aromatic precursors. This paper discusses the logic of general synthetic design for lycoricidine, narciclasine, pancratistatin, and 7-deoxypancratistatin. Experimental details are provided for the recently accomplished syntheses of narciclasine, ent-7-deoxypancratistatin, and 10b-epi-deoxypancratistatin via a new and selective opening of a cyclic sulfate over aziridines followed by aza-Payne rearrangement. The structural core of 7-deoxypancratistatin has also been degraded to a series of intermediates in which the amino inositol unit is cleaved and deoxygenated in a homologous fashion. These truncated derivatives and the compounds from the synthesis of the unnatural derivatives have been tested against six important human cancer cell lines in an effort to further develop the understanding of the mode of action for the most active congener in this group, pancratistatin. The results of the biological activity testing as well as experimental, spectral, and analytical data are provided in this manuscript for all relevant compounds.

Studies on the narciclasine alkaloids: Total synthesis of (+)- narciclasine and (+)-pancratistatin

Enantioselective total syntheses of the antimmor alkaloids, (+)- narciclasine and (+)-pancratistatin, are reported. These syntheses feature a stereo- and regiocontrolled aryl enamide photocyclization to construct a common, advanced intermediate possessing a transfused BC substructure. Differential functional group interchange in the C-ring of this phenanthridone core structure allows for the production of the two target natural products in enantiomerically pure form.

A short chemoenzymatic synthesis of (+)-narciclasine

The title alkaloid has been synthesized in eight operations from dibromobenzene and ovanillin, via enzymatic oxidation of the former compound, Suzuki coupling and a Bischler-Napieralski type cyclization as the key transformations.