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DOI: 10.1016/S0040-4020(01)88129-1

Source and publish data:

Tetrahedron p. 687 - 694 (1992)

Update date:2022-07-30

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Authors:

Boissin, PartrickBoissin, Partrick

Dhal, RobertDhal, Robert

Brown, EricBrown, Eric

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Article abstract of DOI:10.1016/S0040-4020(01)88129-1

(-)-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.

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Full text of DOI:10.1016/S0040-4020(01)88129-1

Products guided by the article

Product name:2(3H)-Furanone, 4-[bromo[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyphenyl]meth yl]dihydro-

Cas No:140193-24-4

140193-24-4

R&D Labs maybe for 140193-24-4

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