54781-87-2

Upstream product

• 571-70-0 (13aS,14S)-14-hydroxytylophorine 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 4897-68-1 2-iodo-4-methoxybromobenzene 
• 1260216-21-4 7-(3',4',5-trimethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine 
• 916263-12-2 2-bromo-3',4',5-trimethoxy-1,1'-biphenyl 
• 93876-11-0 2,3,6-trimethoxyphenanthrene-9-carbaldehyde 
• 30062-39-6 2,3,6-trimethoxyphenanthrene-9-carboxylic acid 
• 30062-14-7 2,3,6-trimethoxy-9-(hydroxymethyl)phenanthrene 
• 50-00-0 formaldehyd 
• 100088-44-6 2-((2,3,6-trimethoxyphenanthren-9-yl)methyl)pyrrolidine 
• 84416-06-8 6-(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-7-(4-methoxyphenyl)indolizine 
• 1043913-75-2 3,6,7-trimethoxy-12,13,13a,14-tetrahydrodibenzo[f,h]pyrrolo-[1,2-b]isoquinolin-9(11H)-one 

Relevant academic research and scientific papers

Modular Syntheses of Phenanthroindolizidine Natural Products

A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.

PHENANTHROINDOLIZIDINE AND PHENANTHROQUINOLIZIDINE ALKALOID HAVING A HYDROXYL GROUP ON THE PHENANTHRENE RING THEREOF, PREPARATION METHOD AND USE THEREOF

A phenanthroindolizidine and phenanthroquinolizidine alkaloid having a hydroxyl group on the phenanthrene ring thereof was synthesized, which exhibits potent activity as an anticancer agent against, such as breast cancer, lung cancer, and prostate cancer.

Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines

Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels-Alder cycloadducts followed by aryl-aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments. A systematic study of the effects of the phenanthrene substitution pattern on the anticancer activity against three human cancer cell lines was discussed. (Chemical Equation Presented).

Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization

A concise and modular synthesis of phenanthroindolizidine alkaloids was achieved by combining iodoaminocylization with a free radical cyclization approach. The route described allowed the preparation of (±)-tylophorine, (±)-antofine, and (±)-deoxypergularinine in six steps. When commercially available l-prolinol was used as a chiral building block, (S)-(+)-tylophorine was also synthesized in 49% yield and >99% ee over five linear steps.

Total synthesis of phenanthroindolizidine alkaloids through an amidyl radical cascade/rearrangement reaction

A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanth

SALTS OF 13A-(S)DESOXYTYLOPHORININE, PREPARATION METHODS AND PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

The present invention relates to the salts of (+)-13a-(S)-deoxytylophorinine represented by the general formula (I), the preparation method thereof, the pharmaceutical compositions containing them, and their use as medicaments for prevention and/or treatment of cancer and/or inflammation disease.

Synthesis of tylocrebrine and related phenanthroindolizidines by VOF 3-mediated oxidative aryl-alkene coupling

A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

Efficient and chirally specific synthesis of phenanthro-indolizidine alkaloids by parham-type cycloacylation

A concise, efficient and modular route involving Parhamtype cycloacylation as the key step has been used to synthesize six enantiopure phenanthro- indolizidine alkaloids 1a-c. The preparation of enantiomerically pure tylophora alkaloids and their seco analogues on a large-scale is now feasible. The alcohol intermediates 8a-c, which are difficult to prepare by other synthetic methodologies, have been synthesized by a metallation-cyclization-reduction sequence in excellent yields.

PHENANTHROINDOLIZIDINE ANALOGUES

Treatment of coronavirus infection with phenanthroindolizidine analogues.

Iron(III) chloride-based mild synthesis of phenanthrene and its application to total synthesis of phenanthroindolizidine alkaloids

Iron(III) chloride has been used to prepare polymethoxy-substituted phenanthrene-9-carboxylic acid via intramolecular oxidative coupling at room temperature in excellent yields. Mild reaction conditions and the use of environmentally friendly FeCl3/