5447-65-4

Basic information

• Product Name: O-diacetyl-(+/-)-α-conidendrine
• CAS NO: 5447-65-4
• Molecular Weight: 440.45
• Mol File: 5447-65-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: O-diacetyl-(+/-)-α-conidendrine(CAS DataBase Reference)
• NIST Chemistry Reference: O-diacetyl-(+/-)-α-conidendrine(5447-65-4)
• EPA Substance Registry System: O-diacetyl-(+/-)-α-conidendrine(5447-65-4)

Safety Data

• Hazardous Substances Data: 5447-65-4(Hazardous Substances Data)

Upstream product

• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 127951-04-6 (+/-)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-05-7 (+/-)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-03-5 (+/-)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 911805-41-9 (+/-)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-00-2 (+/-)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 84755-40-8 (hydroxy-4 methoxy-3 benzyl)-4 dihydro-3H-furannone-2 
• 140193-24-4 (+/-)-3-<α-Bromo-4-(tertio-butyl dimethylsiloxy)-3-methoxybenzyl>butan-4-olide 
• 140193-23-3 (+/-)-3-<(4-Tertio-butyl dimethylsiloxy)-3-methoxybenzyl>butan-4-olide 
• 105783-68-4 O-dibenzyl methyl epi-1-(+/-)-α-conidendral 
• 89067-60-7 (d,l)-O-dibenzyl α-conidendrine 
• 105783-67-3 O-dibenzyl epi-1-(+/-)-α-conidendral 
• 71724-99-7 methyl epi-1-(+/-)-α-conidendral 
• 89067-57-2 (benzoxy-4 methoxy-3)benzyl-2(benzoxy-4 methoxy-3 α,α-propylenedithio)benzyl-3 butanolide 

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.