10.1021/ol800437s.s002
Antonio Salomone
Antonio
Salomone
Vito Capriati
Vito
Capriati
Saverio Florio
Saverio
Florio
Renzo Luisi
Renzo
Luisi
Michael Addition of Ortho-Lithiated Aryloxiranes to α,β-Unsaturated Malonates: Synthesis of Tetrahydroindenofuranones
American Chemical Society
2008
Michael Addition
alkylidene malonates
analogue
Aryloxirane
Michael addition
methodology
oxirane
synthesis
Tetrahydroindenofuranone
epipodophyllotoxin
nucleophilic
lactonization
Malonate
tetrahydroindenofuranone
Synthesi
aryloxirane
Unsaturated
2008-05-15 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Michael_Addition_of_Ortho_Lithiated_Aryloxiranes_to_Unsaturated_Malonates_Synthesis_of_Tetrahydroindenofuranones/2939080
A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.