Synthesis of spirolactones by 1, 3??dipolar cycloadditions to methyl (S)??3??[(E)??cyanomethylidene]??2??oxotetrahydrofuran??5??carboxylate

…, J Svete, L Golič, A Meden, B Stanovnik

Index: Pirc, Samo; Recnik, Simon; Skof, Marko; Svete, Jurij; Golic, Ljubo; Meden, Anton; Stanovnik, Branko Journal of Heterocyclic Chemistry, 2002 , vol. 39, # 2 p. 411 - 416

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Citation Number: 14

Abstract

Treatment of methyl (S)-5-[(E)-(dimethylamino) methylidene]-2-oxotetrahydrofuran-5- carboxylate (2) with potassium cyanide in acetic acid gave (S)-5-[(E)-cyanomethylidene]-2- oxotetrahydrofuran-5-carboxylate (3), which was used as chiral dipolarophile in 1, 3-dipolar cycloadditions. Reactions of 3 with diazomethane (4) and nitrile oxides 5a–c afforded spirolactones 6–8 in 24–34% diastereomeric excess, while with diazomethane (4) in the ...

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