138223-79-7Relevant academic research and scientific papers
A concise synthesis of (-)-conduritol F from L-quebrachitol via AlCl3-n-Bu4NI mediated demethylation
Akiyama, Takahiko,Shima, Hiroaki,Ozaki, Shoichiro
, p. 5593 - 5596 (1991)
(-)-Conduritol F was prepared starting from naturally occurring cyclitol, L-quebrachitol, in 5 steps via AlCl3-Bu4NI mediated chemoselective demethylation of the methyl ether. A preparation of (+)-conduritol B was also described.
Synthesis of (-)-conduritol F, (+)-conduritol B, cyclophellitol from L- quebrachitol
Akiyama,Shima,Ohnari,Okazaki,Ozaki
, p. 3760 - 3767 (2007/10/02)
The methyl ether of cyclitols with vicinal hydroxyl group was cleaved chemoselectively in preference to both cis-and trans-cyclohexylidene moieties by AlCl3-n-Bu4NI to afford parent alcohols in good yields. (-) Conduritol F was prepared from L-quebrachitol, an optically active cyclitol from the serum of rubber trees, in five steps by use of the demethylation reaction. The first chiral synthesis of (+)-conduritol B and the total synthesis of cyclophellitol, a novel β-glucosidase inhibitor, are described.
