935396-15-9Relevant academic research and scientific papers
A formal synthesis of the C1-C9 fragment of amphidinolide C employing the tamaru reaction
Paudyal, Mahesh P.,Rath, Nigam P.,Spilling, Christopher D.
, p. 2954 - 2957 (2010)
Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)2 gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded α,β-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F.
Concise Synthesis of a New Chiral Cyclopentenone Building Block for Prostaglandins and their Derivatives
?urawiński, Remigiusz,?ukasik, Beata
, p. 2612 - 2620 (2019)
(4R,5R)-4,5-O-isopropylidene-2-(dimethoxyphosphoryl)cyclopen-2-enone was obtained in enantiomerically pure form in four steps starting from commercially available 2,3-O-isopropylidene-D-erythronolactone. The key steps involved are diastereoselective lactone ring opening leading in a one-pot procedure to the ε-silyloxy Weinreb-type amide, and the cyclopentenone ring formation by the rhodium catalyzed carbenoid cyclization of the corresponding ε-silyloxy-α-diazo-β-ketophosphonate followed by the elimination of tert-butyldimethylsilanol. During the synthetic study on the construction of the cyclopentanone ring by the intramolecular nucleophilic substitution reaction of an anion generated from ε-bromo-β-ketophosphonate, the formation of cyclopropane derivative was observed. This stereochemical outcome was rationalized using quantum chemical calculations.
