697803-44-4

Upstream product

• 6451-86-1 5-benzyloxy-2-bromo-4-methoxybenzaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 2973-59-3 2-bromoisovanillin 
• 621-59-0 isovanillin 
• 697803-43-3 (E)-3-benzyloxy-6-bromo-4-methoxy-β-chlorostyrene 

Downstream Products

• 1373919-40-4 4-(benzyloxy)-5-methoxy-2-vinylbenzonitrile 
• 1373919-66-4 (R)-5-(benzyloxy)-3-(hydroxymethyl)-6-methoxyisobenzofuran-1(3H)-one 
• 160857-70-5 (3-benzyloxy-6-bromo-4-methoxyphenethylimino)triphenylphosphorane 
• 160857-67-0 8-benzyloxy-5-bromo-7-methoxy-1-(3-nitro-4-methoxybenzyl)-3,4-dihydroisoquinoline 
• 158837-95-7 8-Benzyloxy-7-methoxy-1-(4-methoxy-3-nitro-benzyl)-3,4-dihydro-isoquinoline 
• 158837-97-9 1-(3-Azido-4-methoxy-benzyl)-8-benzyloxy-7-methoxy-3,4-dihydro-isoquinoline 
• 160857-66-9 5-bromo-8-benzyloxy-1-(3,4-dimethoxybenzyl)-7-methoxy-3,4-dihydroisoquinoline 
• 158837-99-1 8-Benzyloxy-1-(3,4-dimethoxy-benzyl)-7-methoxy-3,4-dihydro-isoquinoline 
• 158837-96-8 5-(8-Benzyloxy-7-methoxy-3,4-dihydro-isoquinolin-1-ylmethyl)-2-methoxy-phenylamine 
• 697803-46-6 1-(3,4-Dimethoxy-benzyl)-7-methoxy-3,4-dihydro-isoquinolin-8-ol 
• 479-39-0 (+)-cularine 
• 104420-84-0 (+)-Enneaphylline 
• 55323-56-3 2-(5-benzyloxy-2-bromo-4-methoxyphenyl)ethanol 

Relevant academic research and scientific papers

CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: A facile entry to 3-substituted chiral phthalides

The asymmetric dihydroxylation (AD) of o-cyano cinnamates and styrene derivatives leads to efficient construction of chiral phthalide frameworks in high optical purities. This unique reaction is characterized by unusual synergism between CN and osmate groups resulting in rate enhancement of the AD process. The method is amply demonstrated by the synthesis and the structural/stereochemical assignment of the natural products.

Diastereoselective Synthesis of Cularine Alkaloids via Enium Ions and an Easy Entry to Isoquinolines by Aza-Wittig Electrocyclic Ring Closure

In preliminary communications, we reported the diastereoselective synthesis of cularine and sarcocapnine via the intramolecular ring closure of nitrenium and oxenium ions, a new highly diastereoselective reductive methylation with (+)-8-phenylmenthyl chloroacetate followed by reduction with sodium borohydride, and a facile entry to the isoquinoline precursors by aza-Wittig electrocyclic ring closure. We now report the full details of the syntheses of (+)-O-demethylcularine, (+)-cularine, (+)-sarcocapnidine, (+)-sarcocapnine, and (+)-crassifoline and describe different methods of synthesis of their precursors.