79831-87-1

Upstream product

• 3934-86-9 methyl 3,4-dihydroxy-5-methoxybenzoate 
• 100-44-7 benzyl chloride 
• 5438-36-8 5-iodovaniline 
• 3934-87-0 5-hydroxyvanillin 
• 70845-72-6 methyl 4,5-bisbenzyloxy-3-methoxybenzoate 
• 121-33-5 vanillin 

Downstream Products

• 79624-50-3 4,5-bisbenzyloxy-3-methoxybenzyl chloride 
• 651340-03-3 1,2-bis(benzyloxy-5-(bromomethyl)-3-methoxybenzene 
• 86761-99-1 4,5-bisbenzyloxy-3-methoxyphenylacetonitrile 
• 79624-47-8 2-(4,5-bisbenzyloxy-3-methoxyphenyl)ethylamine 
• 1026980-58-4 4-(4-benzyloxy-3-methoxy-benzyl)-3-(3,4-bis-benzyloxy-5-methoxy-benzyl)-dihydro-furan-2-one 

Relevant academic research and scientific papers

Biosynthesis of yatein in Anthriscus sylvestris.

Little is known about the biosynthesis of yatein, in spite of its importance as a typical heartwood lignan and a key biosynthetic intermediate of the antitumor lignan podophyllotoxin. The present study, based on individual administration of [13C]phenylalanine and deuterium labelled lignans and simultaneous administration of two distinct lignans labelled with deuterium atoms to Anthriscus sylvestris, established the two independent branch pathways from matairesinol, one to afford yatein via thujaplicatin, 5-methylthujaplicatin, and 4,5-dimethylthujaplicatin and the other to bursehernin via pluviatolide. The latter pathway did not lead to yatein, eliminating the presence of a metabolic grid from matairesinol to yatein.

Biosynthesis. Part 24. Speculative Incorporation Experiments with 1-Benzylisoquinolines and a Logical Approach via C6-C2 and C6-C3 Precursors to the Biosynthesis of Hasubanonine and Protostephanine

Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly.Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6-C2 biogenetic units.The subsequent failure of further 1-benzyltetrahydroisoquinolines and bisphenethylamines to be incorporated suggested the intermediacy of either (a) modified 1-benzylisoquinolines or (b) trioxygenated C6-C2 building blocks.Precursors designed to examine the first possibility, such as 1-benzyl-3,4-dihydroisoquinolines or 1-benzyl-1-carboxytetrahydroisoquinolines, were not incorporated into (1) and (2) whereas two 3',4',5'-trioxygenated 2-phenylethylamines were incorporated.These findings allow further delineation of the requirements for later precursors of the alkaloids (1) and (2).