70670-14-3Relevant academic research and scientific papers
Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors
Hiyama,Reddy,Minami,Hanamoto
, p. 350 - 363 (2007/10/02)
Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.
Use of 1,3-dioxin-4-ones and related compounds in synthesis. XLIV. Asymmetric aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines: Use of tartaric acid-derived (acyloxy)borane complex as the catalyst
Sato,Sunami,Sugita,Kaneko
, p. 839 - 845 (2007/10/02)
A novel enantioselective synthesis of 1,3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1,3-dioxin-4-one with achiral aldehydes.
Enzyme-catalyzed Lactonization of Methyl (+/-)-(E)-3,5-Dihydroxy-7-phenyl-6-heptenoates. - A Comparison of the Behaviour of syn- and anti-Compounds
Henkel, Birgitta,Kunath, Annamarie,Schick, Hans
, p. 153 - 156 (2007/10/02)
3-Hydroxy lactones with a high enantiomeric excess were obtained by the lipase-catalyzed enantioselective lactonization of racemic syn- and anti-3,5-dihydroxy carboxylic esters.The (5S)-lactones were formed predominantly from both diols with pancreatin as
SYNTHESIS OF THE 5,6-DIHYDRO-2-PYRONE MOIETY OF (+)-ANAMARIN
Gillard, Frederic,Heissler, Denis,Riehl, Jean-Jacques
, p. 2291 - 2296 (2007/10/02)
The α,β-unsaturated δ-lactone (+)-goniothalamin (18E) and its Z-isomer (18Z), which contain the lactonic moiety of (+)-anamarin (1), have been synthesized from the known 1,2-O-isopropylidene 3-deoxy-α-D-glucofuranose (7).In the key step, methyl 3,5-dideoxy-β-D-glucofuranuronate (15) was treated with benzylidenetriphenylphosphorane in dimethyl sulphoxide to give the E- and Z-β-hydroxy δ-lactones (17).These were then transformed into the 5,6-dihydro-2-pyrones (18), and also into the aldehyde (20), intended for use in a total synthesis of (+)-anamarin (1).
SYNTHESES OF ARGENTILACTONE 11 AND GONIOTHALAMIN 15
O'Connor, Brian,Just, George
, p. 5201 - 5202 (2007/10/02)
Syntheses of (-)-(5R)-argentilactone 11 and (+)-(5R)-goniothalamin 15 are described starting from olefin 4.
