62427-70-7Relevant articles and documents
Asymmetric synthesis of machilin C and its analogue
Xia, Yamu,Wang, Wei
experimental part, p. 630 - 636 (2011/10/19)
Full details of the asymmetric total synthesis of erythro-8-O-4′-neolignan, machilin C, and its analogue perseal A are reported. The synthesis was involved in the Sharpless dihydroxylation reaction that occurred with excellent asymmetric induction, and the Mitsunobu reaction which occurred with inversion of the absolute configuration from the threo to the erythro isomer. The synthesis was achieved from simple vanillin in eight to twelve steps.
Regioselective cleavage reaction of the aromatic methylenedioxy ring. V. Cleavage with sodium alkoxides-alcohols, potassium tert-butoxide-alcohols, dimsyl anion-methyl alcohol, metallic sodium-alcohols, and sodium cyanide in dipolra aprotic solvents
Imakura,Okimoto,Konishi,Hisazumi,Yamazaki,Kobayashi,Yamashita
, p. 1691 - 1696 (2007/10/02)
The reaction of aromatic methylenedioxy compounds containing electron-withdrawing groups with dimsyl anion-methyl alcohol, potassium tert-butoxide-alcohols, and metallic sodium-alcohols in dimethyl sulfoxide (DMSO), and with sodium alkoxides-alcohols in hexamethylphosphoramide, gave 3- and 4-hydroxybenzene derivatives in good yield by regioselective attack of the alkoxide ions on the methylenedioxy ring. The formation mechanism of alkoxide ions and the effect of DMSO in the cleavage reaction of the methylenedioxy ring are discussed on the basis of proton nuclear magnetic resonance (1H-NMR) spectra. The reactions of aromatic methylenedioxy compounds (3 and 22) with sodium cyanide in dipolar aprotic solvents gave 4-cyano-3-hydroxybenzene derivatives (23 and 24) by regioselective attack of the cyanide ion on the methylenedioxy ring. The reactions of aromatic methylenedioxy compounds (28-30) containing no electron-withdrawing group with MeONa-MeOH in dipolar aprotic solvents gave non-regioselective cleavage products (31 and 34).
