152785-40-5Relevant academic research and scientific papers
2-Fluoro-2-buten-4-olide, a New Fluorinated Synthon. Preparation; 1,2-, 1,4- And Tandem Additions
Kví?ala, Jaroslav,Plocar, Jakub,Vlasáková, R??ena,Paleta, Old?ich,Pelter, Andrew
, p. 986 - 988 (1997)
2-Fluoro-2-buten-4-olide (1) was prepared either by transformation of D-erythronolactone or by Wittig-Horner reaction of ethyl (diethoxyphosphoryl)fluoroacetate with acetoxyacetaldehyde followed by ring closure. It can be transformed by 1,2-addition of nitrogen or hard carbon nucleophiles to fluorinated hydroxyamides or diols and by 1,4-addition of soft carbon nucleophiles to β-alkylated 2-fluorobutan-4-olides. Tandem addition leads to α,β disubstituted 2-fluorobutan-4-olides which are intermediates for the synthesis of fluorinated lignans.
General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides
Matsuoka, Seiya,Nakamura, Kayo,Ohmori, Ken,Suzuki, Keisuke
, p. 1139 - 1156 (2019/02/26)
A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.
Preparation of intermediates for fluorinated lignans by conjugated and tandem additions on 3-fluorofuran-2(5H)-one
Kvicala, Jaroslav,Vlasakova, Ruzena,Plocar, Jakub,Paleta, Oldrich,Pelter, Andrew
, p. 772 - 788 (2007/10/03)
Two syntheses of 3-fluorofuran-2(5H)-one (1) based on Wittig-Horner reaction of ethyl (diethoxyphosphoryl)fluoroacetate (15) with 2-oxoethyl acetate (16) or on transformation of D-erythronolactone (10) are given. 3-Fluorofuran-2(5H)-one (1) and ethyl 2-fluorobut-2-enoate (2) undergo conjugate addition with soft nucleophiles based on arenecarboxaldehyde dithioacetals 7 to form 2-fluorolactones 3 and 2-fluoroalkanoates 4. Intermediate enolates can be trapped in the sense of tandem addition with arenecarboxaldehydes 8 or (arylmethyl)bromides 9 to form intermediates 5 and 6 for fluorolignans. Although the conjugate addition proceeds with low stereoselectivity yielding mixture of both diastereoisomers, the electrophile in tandem addition attacks the intermediary fluoroenolate exclusively anti to its bulky β-substituent in good accord with non-fluorinated furan-2(5H)-ones.
