61302-92-9

Usage

Uses

Used in Medicinal Chemistry:
(13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline is used as a research compound in medicinal chemistry for its potential therapeutic applications and biological effects. Its unique structure and properties may offer insights into the development of new drugs and treatments.

Upstream product

• 26503-67-3 (+/-)-6,7-di(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-indolizine 
• 55171-60-3 2-bromo-3,4-dimethoxybenzylaldehyde 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 85010-22-6 2-(3,4-dimethoxyphenyl)-3,4-dimethoxybenzaldehyde 
• 1588418-51-2 2-(3,4-dimethoxyphenyl)-3,4-dimethoxybenzyl alcohol 
• 1588418-52-3 C₁₇H₁₉BrO₄ 
• 1588418-53-4 C₂₂H₂₄O₆ 
• 1588418-54-5 C₂₂H₂₄O₆ 
• 1588418-55-6 C₂₀H₂₀O₅ 
• 2973-58-2 2-bromoisovanillin 
• 2859-78-1 4-Bromoveratrole 
• 621-59-0 isovanillin 
• 40972-86-9 (2,3-dimethoxyphenyl)boronic acid 
• 89978-46-1 4-bromo-5-iodoveratrole 

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.

Collective asymmetric synthesis of (-)-Antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary

A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.

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.

Compounds and compositions for treating infection

Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.

Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination

(Chemical Equation Presented) The enantioselective synthesis of (S)-(+)-tylophorine, a potent cancer cell growth inhibitor, has been accomplished in eight steps from commercially available 3,4-dimethoxybenzyl alcohol. A copper (II)-catalyzed enantioselective intramolecular alkene carboanimation was employed as the key step to construct the chiral indolizidine ring.

General Synthesis of Phenanthroindolizidine, Phenanthroquinolizidine, and Related Alkaloids: Preparation of (+/-)-Tylophorine, (+/-)-Cryptopleurine, (+/-)-Septicine, and (+/-)-Julandine

A general synthetic route to the pentacyclic phenanthro class and related indolizidine and quinolizidine alkaloids via β-amino ketone intermediates is reported.The synthesis of tylophorine, cryptopleurine, septicine, and julandine, in racemic forms, has been described.Synthetic steps in the preparation of these alkaloids involve 1,3-dipolar cycloadditions of the cyclic nitrones as a common feature followed by crucial ring closure by aldol reactions and photolyses.