805240-03-3

Upstream product

• 805239-89-8 acetic acid 5-formyl-2-methanesulfonyloxy-phenyl ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 805239-90-1 (E)-3-(3-acetoxy-4-methanesulfonyloxy-phenyl)-acrylic acid methyl ester 
• 186581-53-3 diazomethane 

Downstream Products

• 805239-91-2 (E)-3-(3-allyloxy-4-methanesulfonyloxy-phenyl)-acrylic acid methyl ester 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 1053742-45-2 C₄₉H₄₄F₆O₁₀S 
• 805239-99-0 C₄₁H₄₂O₈ 
• 805239-95-6 methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester 
• 805239-97-8 Methanesulfonic acid 3-allyl-2-ethoxy-4-[(R)-1-((2S,4S,5S,10S)-8,8,10-trimethyl-2-phenyl-1,3,7,9-tetraoxa-spiro[4.6]undec-4-yl)-allyl]-phenyl ester 
• 695230-84-3 methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester 
• 695230-90-1 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenol 
• 805239-93-4 (E)-3-(2-allyl-3-ethoxy-4-methanesulfonyloxy-phenyl)-acrylic acid methyl ester 
• 805239-94-5 methanesulfonic acid 3-allyl-2-ethoxy-4-((E)-3-hydroxy-propenyl)-phenyl ester 
• 805239-88-7 methanesulfonic acid 3-allyl-2-ethoxy-4-((E)-3-bromo-propenyl)-phenyl ester 
• 805239-92-3 (E)-3-(2-allyl-3-hydroxy-4-methanesulfonyloxy-phenyl)-acrylic acid methyl ester 
• 695230-92-3 methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(S)-hydroxy-((4S,6S)-4-hydroxymethyl-2,2,6-trimethyl-[1,3]dioxan-4-yl)methyl]-allyl-phenyl ester 
• 823788-11-0 (E)-methyl 3-(3-methoxy-4-((methylsulfonyl)oxy)phenyl)acrylate 

Relevant academic research and scientific papers

Diastereoselective phenol para-alkylation: Access to a cross-conjugated cyclohexadienone en route to resiniferatoxin

(Chemical Equation Presented) We document a route for the synthesis of a densely functionalized spiro-fused 2,5-cyclohexadienone as an intermediate for the synthesis of resineferatoxin. The strategy is based on an unprecedented diastereoselective, intramolecular phenol para-alkylation to a cross-conjugated cyclohexadienone. In the course of these synthetic studies we developed rapid access to a chiral nitrile possessing a quaternary stereocenter and disclose an unusual acetal rearrangement from a dioxane, which favors the corresponding dioxepane.

BIOSYNTHESIS OF PODOPHYLLUM LIGNANS - I. CINNAMIC ACID PRECURSORS OF PODOPHYLLOTOXIN IN PODOPHYLLUM HEXANDRUM

Feeding experiments in Podophyllum hexandrum plants have established that phenylalanine, cinnamic acid and ferulic acid are good precursors of the two major aryltetralin lignans podophyllotoxin and 4'-demethylpodophyllotoxin.Sinapic and 3,4,5-trimethoxycinnamic acids were poorly utilized, showing that the substitution pattern of the pendent aryl ring is built up after coupling of the two phenylpropane units.Degradation studies on podophyllotoxin derived from ferulic acid show that the two halves of the lignan molecule are equally labelled supporting a biosynthetic sequence involving oxidative coupling of two similar phenylpropane precursors having the substitution pattern of ferulic acid.Although 3,4-methylenedioxycinnamic acid was readily incorporated, degradative studies prove that this compound is not incorporated intact, but via a metabolic sequence in which the methylenedioxy carbon atom enters the C1-pool and then labels the methylenedioxy and methoxyl substituents of podophyllotoxin.The rest of the skeleton is incorporated via ferulic acid, presumably by way of caffeic acid.Key Word Index - Podophyllum hexandrum; Podophyllaceae; aryltetralin; lignans; biosynthesis; podophyllotoxin.