140193-27-7

Basic information

• Product Name: (-)-O-6-Benzyl-α-conidendrine
• Synonyms: (-)-O-6-Benzyl-α-conidendrine
• CAS NO: 140193-27-7
• Molecular Weight: 446.5
• Mol File: 140193-27-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-O-6-Benzyl-α-conidendrine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-O-6-Benzyl-α-conidendrine(140193-27-7)
• EPA Substance Registry System: (-)-O-6-Benzyl-α-conidendrine(140193-27-7)

Safety Data

• Hazardous Substances Data: 140193-27-7(Hazardous Substances Data)

Upstream product

• 127951-03-5 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 127951-01-3 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-00-2 (3R)-(+)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 127951-04-6 (2R,3R)-(6R,S)-(+)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 

Downstream Products

• 25047-22-7 (-)-O-Diacetyl-α-conidendrine 
• 518-55-8 conidendrin 

Relevant articles and documents

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(-)-α-Conidendrin 1 was synthesized according to a general reactionscheme that could be applied to other retrolignans as well. Thus, treatment of the optically active β-benzyl-γ-butyrolactone (R)-(+)-4 with NBS, followed with benzyl alcohol, selectively introduced a benzyloxy group in the benzylic position and afforded the mixture of epimers 7. α-Alkylation of the lithium enolate of the corresponding silyl ethers 10, with O-benzylvanillyl bromide 11, gave the trans disubstituted lactones 13 (2 epimers). Catalytic hydrogenolysis (Pd-C) of 13 selectively split the aryl benzyl ether linkage, and gave the compounds 14. Intramolecular Friedel-Crafts cyclization of the latter, using the benzyloxy group as the leaving group, was induced with BF3-Et2O and afforded (-)-α-conidendrin 1 in 36% overall yield from methyl α-vanillylhemis uccinate (R)-(+)-17.