115071-50-6Relevant articles and documents
Synthesis of Naturally Occurring (+/-)-7,3'-Dihydroxy-4'-methoxyisoflavanone and Some Isoflavanones Related to Natural 6,7-Dimethoxy-3',4'-methylenedioxyisoflavanone
Jain, A. C.,Bambah, P. K.
, p. 628 - 633 (2007/10/02)
2,4,3'-Trihydroxy-4'-methoxydesoxybenzoin (2) on treatment with two mol of ethoxymethyl chloride followed by one mol of ethoxymethyl chloride yields the α-hydroxyketone (4) which undergoes cyclization with 4 percent EtOH-Na2CO3 to afford 7,3'-diethoxymethoxy-4'-methoxyisoflavanone (5).Deprotection of 5 with 10 percent MeOH-HCl yields the naturally occurring 7,3'-dihydroxy-4'-methoxyisoflavanone (1a).Similarly 7-methoxy-3',4'-methylenedioxy-(9a)-, 5,7-dimethoxy-3',4'-methylenedioxy-(9b), 6,7-dimethoxy-(9c), and 7-hydroxy-3',4'-methylenedioxy-(14)-isoflavanones have been synthesized starting from the corresponding desoxybenzoins (7a, 7b, 7c and 10 respectively) via α-hydroxymethylation to yield the carbinols (8a, 8b, 8c and 12 respectively) and then cyclization to give the corresponding isoflavanones.The isoflavanone 14 is obtained by treating 13 with 10 percent MeOH-HCl.
