Stereoselective Synthesis of Naturally Occurring α-Methylenebis-γ-butyrolactones: An Application of Novel Oxiranyl “Remote” Anions
- 1 June 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (13) , 4692-4694
- https://doi.org/10.1021/jo010259f
Abstract
Stereospecific deprotonation of the epoxy proton at the β-position of the α,β-epoxy esters 5 and 6 yielded oxiranyl “remote” anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones 11 and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring α-methylenebis-γ-butyrolactones, 1.Keywords
This publication has 9 references indexed in Scilit:
- Metalated Epoxides as Carbenoids. Solvent Effect on Competing Intramolecular C−H and Intermolecular C−Li Insertions in α-Alkoxy Epoxide SystemsThe Journal of Organic Chemistry, 1999
- Hemi-Labile Ligands in Organolithium Chemistry: Rate Studies of the LDA-Mediated α- and β-Metalations of EpoxidesJournal of the American Chemical Society, 1999
- An aldol - bislactonization route to α-methylene bis-γ-butyrolactonesTetrahedron, 1998
- Complex-Induced Proximity Effects: Stereoselective Carbon−Carbon Bond Formation in Chiral Auxiliary Mediated β-Lithiation−Substitution Sequences of β-Substituted Secondary CarboxamidesThe Journal of Organic Chemistry, 1998
- Regioselective, Diastereoselective, and Enantioselective Lithiation−Substitution Sequences: Reaction Pathways and Synthetic ApplicationsAccounts of Chemical Research, 1996
- Oxiranyl Anions and Aziridinyl AnionsChemical Reviews, 1996
- Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromaticsChemical Reviews, 1990
- Stereo- and regiocontrol by complex induced proximity effects: reactions of organolithium compoundsAccounts of Chemical Research, 1986
- Simple routes to sarkomycinJournal of the American Chemical Society, 1984