30061-35-9

Upstream product

• 26503-67-3 (+/-)-6,7-di(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-indolizine 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 40972-86-9 (2,3-dimethoxyphenyl)boronic acid 
• 89978-46-1 4-bromo-5-iodoveratrole 
• 1260216-14-5 7-(2',3',4,5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine 
• 1260216-09-8 2'-bromo-2,3,4',5'-tetramethoxy-1,1'-biphenyl 

Relevant academic research and scientific papers

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.

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.

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.

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.