70191-79-6

Upstream product

• 70148-37-7 (S)-(-)-4-(3,4-methylenedioxybenzyl)dihydrofuran-2(3H)-one 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 70148-33-3 trans-(S)-2-piperonylidene-4-benzyloxymethyl-4-butanolide 
• 42170-41-2 ethyl 1-(3,4,5-trimethoxybenzoyloxy)formate 
• 120-57-0 piperonal 
• 118-41-2 Eudesmic acid 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 123976-18-1 trans-3,3-dichloro-4-(3,4-methylenedioxyphenyl)methyl-5-p-tolylthio-4,5-dihydrofuran-2(3H)-one 
• 123976-19-2 4-(3,4-methylenedioxyphenyl)methyl-5-p-tolylthio-4,5-dihydrofuran-2(3H)-one 
• 123976-15-8 (+)-(R)-(E)-1-<3-(3,4-methylenedioxyphenyl)propenyl> p-tolyl sulphoxide 
• 17187-78-9 (+/-) epi-podorhizol 
• 17187-78-9 (+/-) podorhizol 
• 80483-34-7 4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one 

Downstream Products

• 477-51-0 rac-(7'β,8α,8'percentb)-3',4',5'-trimethoxy-4,5-methylenedioxy-2,7'-cyclolignan-9',9-olide 
• 17187-78-9 (+/-) podorhizol 
• 17187-78-9 (+/-) epi-podorhizol 

Relevant academic research and scientific papers

Highly Enantiospecific Synthesis of 4-Alkyl and 4,5-Dialkyl Substituted 4,5-Dihydrofuran-2(3H)-ones from Optically Active (E)- and (Z)-Alk-1-enyl p-Tolyl Sulphoxides: Application to the Synthesis of Lignan Lactones

Stereochemically and optically pure 2-substituted ethylenic p-tolyl sulphoxides (R)-E-(4) and (R)-Z-(4) undergo readily and stereospecifically an additive Pummerer rearrangement reaction with dichloroketene to give trans- and cis-β-alkyl-α,α-dichloro-γ-p-tolylthio-γ-butyrolactone derivatives (5), respectively.Sequential reductive dechlorination and desulphurization lead to (-)-(S)-, from trans-(5), and (+)-(R)-β-alkyl-γ-butirolactones (7), from cis-(5), with a high optical purity, respectively.Reaction of the intermediate tolylthio derivatives (6) with allyltributylstannane gives β-alkyl-γ-allyl-γ-butyrolactones (15) and (16).These sequential reactions can be successfully applied to the synthesis of (+)-(R)-β-piperonylbutyrolactone (20), the key intermediate for the synthesis of antileukemic lignan lactones, in high chemical and optical yields.Acylation of compound (20) with 3,4,5-trimethoxybenzoyl chloride furnishes (+)-podorhizon (21).

(S)-(+)-2-(p-TOLYLSULFINYL)-2-BUTEN-4-OLIDE: AN ENANTIOMERICALLY PURE MICHAEL ACCEPTOR FOR ASYMMETRIC SYNTHESIS OF 3-SUBSTITUTED 4-BUTANOLIDES. (-)-PODORHIZON.

A short, reliable, and practical synthesis of (S)-(+)-2-(p-tolylsulfinyl)-2-buten-4-olide has been developed, and the utility of this Michael acceptor for highly enantiocontrolled synthesis of 3-substituted 4-butanolides has been demonstrated.

SYNTHESES TOTALES ET ETUDES DE LIGNANES BIOLOGIQUEMENT ACTIFS-II. APPLICATION DE L'α-HYDROXYALKYLATION DE β-BENZYL χ-BUTYROLACTONE A LA CREATION DES SQUELETTES PHENYL TETRALINE ET BISBENZOCYCLOOCTADIENES. SYNTHESE TOTALE DU (+/-) PODORHIZOL, DE LA (+/-) P

The use of lithium hexamethyldisilylamide (LHDS) in α-hydroxyalkylation of β-(3,4-methylenedioxybenzyl)-χ-butyrolactone gives high yields of (+/-) podorhizol and (+/-) epi-podorhizol as a 1:1 diastereoisomer mixture.Cyclisation of both alcohols using trif