Journal of Organic Chemistry. Vol.66, No.13 (2001), 4692-4694
Suggested Citation
J. Lertvorachon, Y. Thebtaranonth, T. Thongpanchang, P. Thongyoo Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl "remote" anions. Journal of Organic Chemistry. Vol.66, No.13 (2001), 4692-4694. doi:10.1021/jo010259f Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/26508
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Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl "remote" anions
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.
