80299-54-3

Upstream product

• 144709-26-2 2,3-dimethoxy-6-iodobenzamide 
• 246256-89-3 2-(3,4-methylenedioxy-6-iodophenyl)acetic acid 
• 124-40-3 dimethyl amine 
• 56221-41-1 6-iodo-2,3-dimethoxybenzoic acid 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 76202-53-4 (Z)-N-methylhydrastine 
• 55922-35-5 (E)-N-methylhydrastine 
• 51390-68-2 β-hydrastine methiodide 
• 80299-52-1 α-hydrastine methiodide 
• 31971-15-0 N-methylhydrasteine 
• 612845-92-8 3-(diphenylphosphinoyl)-6,7-dimethoxy-2-(4-methoxybenzyl)-2,3-dihydro-1H-isoindol-1-one 
• 612846-05-6 3-hydroxy-6,7-dimethoxy-2-(4-methoxybenzyl)-2,3-dihydro-1H-isoindol-1-one 
• 612846-03-4 6-bromo-2,3-dimethoxy-N-(4-methoxybenzyl)benzamide 

Downstream Products

• 80299-53-2 (E)-fumaridine 

Relevant academic research and scientific papers

Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine

A unified strategy for protecting-group-free synthesis of alkaloids lennoxamine, chilenine, fumaridine, 8-oxypseudoplamatine, and 2-O-(methyloxy)fagaronine is reported. The core isoindolin-1-one and isoquinolin-1-one structures were built by a silver-cata

First total synthesis of fumaridine

The first total synthesis of the alkaloid fumaridine 1a is reported. The key step is the assemblage of the arylmethylene isoindolinone 2a (E) by Horner reaction between the phosphorylated isoindolinone 3a and the suitably substituted benzaldehyde 4. N-Lactam deprotection and concomitant E→Z isomerization complete the synthesis of the title compound.

Secophthalideisoquinolines

The secophthalideisoquinolines can be subdivided into enol lactones, keto acids, diketo acids, and ene lactams.The diastereomeric β- and α-hydrastine methiodides (8 and 9) supply stereoselectively Z and E enol lactones 11 and 12, respectively, in a syn β-elimination process.N-Methylhydrastine (11) reacts under mild conditions with methanol, water, or ammonia to produce keto ester 18, keto acid 17, or hydroxy lactam 36, respectively.Treatment of hydroxy lactam 36 with acid results in rapid loss of water and formation of the Z ene lactam 33.Photoequilibration of 33gives rise to a mixture of Z and E ene lactams 33 and 34.A biogenetic scheme is proposed for the secophthalideisoquinolines which includes the following sequence: classical phthalideisoquinoline -> phthalideisoquinoline N-metho salt -> secophthalide enol lactone -> secophthalide keto acid -> secophthalide diketo acid -> fumariflorine-type alkaloid.Ene lactams 30-33, as well as the hydroxy lactam fumschleicherine (35), are most probably artifacts of isolation.