40599-78-8Relevant articles and documents
New synthesis of (±)2,3-dimethoxyhexahydroberbine
Chatterjee, Asima,Sahu, Arabinda,Saha, Munmun,Banerji, Julie
, p. 121 - 122 (2007/10/03)
The total synthesis of (±)2,3-dimethoxyhexahydroberbine 7 key compound transhexahydroisochroman-3-one 5 has been reported.
Models for Glycoside Hydrolysis. Synthesis and Hydrolytic Studies of the Anomers of a Conformationally Rigid Acetal
Eikeren, Paul van
, p. 4641 - 4645 (2007/10/02)
The methyl acetals of 2-hydroxy-3-oxa-trans-decalin were synthesized as models for conformationally rigid methyl glycosides.The compounds were prepared by Baeyer-Villiger oxidation of trans-hexahydrohydrindan-2-one followed by reduction of the resulting lactone with diisobutylaluminum hydride.Treatment of the hemiacetal with methanol and an acid catalyst afforded a mixture of acetals which were separated by chromatography and identified by NMR.Hydrolytic studies were carried out under a range of acid concentrations and temperatures.The mechanistic implications of the relative hydrolysis rates (axial/equatorial ratio of 1.51+/-0.22) and activation parameters are discussed.