754147-29-0Relevant articles and documents
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.
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 (2007/10/03)
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.
