93219-52-4Relevant academic research and scientific papers
Studies on the Constituents of the Seeds of Hernandia ovigera L. IV. Syntheses of β-Peltatin-A and -B Methyl Ethers from Desoxypodophyllotoxin
Yamaguchi, Hideo,Nakajima, Syunji,Arimoto, Masao,Tanoguchi, Mariko,Ishida, Toshimasa,Inoue, Masatoshi
, p. 1754 - 1760 (2007/10/02)
Two kinds of 4-aryltetralin type lignans, β-peltatin-A methyl ether (I-A) and β-peltatin-B methyl ether (I-B), were synthesized from desoxypodophyllotoxin (DPT), which is available in large quantities from the seeds of Hernandia ovigera L. (Hernandiaceae).The syntheses were achieved via demethylene-DPT (IV), 8-bromo-demethylene-DPT (V) and 8-bromo-DPT (VI).Methylenation of V was carried out successfully by using cesium fluoride and methylene iodide in DMF.Compound I-B was readily obtained by the reaction of VI with cuprous iodide and sodium methoxide in the presence of pyridine.Synthesis of I-A was only achieved by the reaction of lithiated VI with nitrobenzene at -100 deg C in the presence of tetramethylethylene diamine, and I-A was obtained in low yield, together with I-B.Keywords Hernandia ovigera; 4-aryltetralin lignan; desoxypodophyllotoxin (DPT); desoxypicropodophyllin (DPP); 2'-bromo-desoxypodophyllotoxin; 8-bromo-desoxypodophyllotoxin; beta-peltatin-A methyl ether; beta-peltatin-B methyl ether; lithiated desoxypodophyllotoxin; lignan X-ray analysis
