Tetrahedron Letters

Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

CS Maria Del Pilar, N Shankaraiah, LS Santos

Index: Soriano, Maria Del Pilar C.; Shankaraiah, Nagula; Santos, Leonardo Silva Tetrahedron Letters, 2010 , vol. 51, # 13 p. 1770 - 1773

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Citation Number: 14

Abstract

A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine (1a–c), as well as capnoidine and corytensine (2a, b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one- pot approach. The synthesis features the use of imine 13 obtained through Bischler– Napieralsky reaction from amine 11. The addition of ionic liquids as addictives in the ...

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