58894-52-3

Upstream product

• 61038-90-2 (-)-isostegane 
• 64-19-7 acetic acid 
• 57009-70-8 2-(3,4,5-trimethoxyphenyl)-1,3-dithiane 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 72627-52-2 (2S,3S,4S)-(+)-2-piperonyl-3-(3,4,5-trimethoxybenzyl)-4-hydroxymethyl-butan-4-olide 
• 72605-54-0 (+)-(2S,3S,4S)-2-piperonyl-3-(2-(3,4,5-trimethoxyphenyl)-1,3-dithiane-2-yl)-4-benzyloxymethyl-butan-4-olide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 40456-50-6 yatein 
• 76236-35-6 (3S,4S)-(+)-3-(3,4,5-trimethoxybenzyl)-4-hydroxymethyl-butan-4-olide 
• 72627-54-4 (3S,4S)-(+)-2-hydroxy-3-(3',4',5'-trimethoxybenzyl)-4-piperonyl-tetrahydrofurane 
• 76236-36-7 (2S,3S,4S)-(+)-3-(3',4',5'-trimethoxybenzyl)-4-piperonyl-1,2,5-pentanetriol 
• 76236-33-4 (3S,4S)-(+)-3-(2-(3,4,5-trimethoxyphenyl)-1,3-dithiane-2-yl)-4-trityloxymethyl-butan-4-olide 
• 92232-57-0 (3S,4S,5S)-3-Benzo[1,3]dioxol-5-ylmethyl-4-(3,4,5-trimethoxy-benzyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 108-24-7 acetic anhydride 

Downstream Products

• 41451-68-7 (-)-episteganacin 
• 61038-90-2 (+/-)-isostegane 

Relevant academic research and scientific papers

PROCESS TO OBTAIN SYNTHETIC AND SEMI-SYNTHETIC LIGNAN DERIVATIVES, THEIR ANTIPARASITIC ACTIVITIES AND CORRESPONDING PHARMACEUTICAL FORMULATIONS, INCLUDING THE THERAPEUTIC METHOD USING SAID LIGNAN FOR THE TREATMENT OF PARASITOSIS

The invention refers to a process to obtain synthetic and semi-synthetic derivatives of lignans, especially dibenzylbutyrolactonic, tetrahydrofuranic, aryltetralynic, furofuranic and dibenzocyclooctanic lignans obtained by means of partial synthesis and/o

ASYMMETRIC TOTAL SYNTHESIS OF NATURAL (-)- AND UNNATURAL (+)-STEGANACIN DETERMINATION OF THE ABSOLUTE CONFIGURATION OF NATURAL ANTITUMOR STEGANACIN

A virtually complete asymmetric control in the synthesis of 2,3-disubstituted butan-4-olide (10) was demonstrated by employing the butenolide (12) as the chiral acceptor for the conjugate 1,4-addition.Highly efficient asymmetric total synthesis of natural (-)- and unnatural (+)-steganacin was accomplished.The absolute stereostructure of natural antitumor steganacin was determined to be 1.

SYNTHESES TOTALES ET ETUDES DE LIGNANES BIOLOGIQUEMENT ACTIFS. APPLICATION DE L'α-HYDROXYALKYLATION DE β-BENZYL γ-BUTYROLACTONES A LA CREATION DES SQUELETTES PHENYL TETRALINE ET BISBENZOCYCLOOCTADIENE - 4. SYNTHESE TOTALE DE LA (+/-)-STEGANONE ET DE SES C

The biphenyl 16 (obtained from α-bromopiperonal and the aromatic iodide 14 by a modified Ullmann reaction) was cyclized by intramolecular hydroxyalkylation to the isomeric alcohols 17a and 17b.These were oxidized using Jones' reagent, to afford the enol 1

The Ambient Temperature Ullmann Reaction and Its Application to the Total Synthesis of (+/-)-Steganacin

The details of a new method for preparing unsymmetrical biphenyls at room temperature by a modification of the classical Ullmann reaction are discussed.An intramolecularly coordinated organocopper reagent is treated with an aryl iodide bearing a potential coordinating ligand to form the biphenyl.Nitrogen and sulfur have been utilized as ligands and as protecting groups for carbonyls.The application of this methodology to the synthesis of the antileukemic steganacin is detailed.

FIRST ASYMMETRIC TOTAL SYNTHESIS OF (+)-STEGANACIN. DETERMINATION OF ABSOLUTE STEREOCHEMISTRY

(+)-Steganacin was synthesized in a new and highly specific asymmetric pathway based on the novel application of chiral γ-lactone as a chiral synthon.By this synthesis the absolute stereochemistry of natural (-)-steganacin could be determined in unequivoc