123453-95-2Relevant articles and documents
Deracemization of cyclic allyl esters
Trost, Barry M.,Organ, Michael G.
, p. 10320 - 10321 (1994)
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Enzyme catalyzed reverse enantiomeric separation of methyl (±)-3-cyclohexene-1-carboxylate
Tanyeli, Cihangir,Turkut, Engin
, p. 2057 - 2060 (2004)
We describe the differences of hydrolase-type enzymes pig liver esterase (PLE), horse liver esterase (HLE), and porcine pancreatic lipase (PPL) on the hydrolysis of methyl (±)-3-cyclohexene-1-carboxylate to afford both enantiomers with 89% to the resultant enantiomerically pure (S)-(-)-3- cyclohexene-1-carboxylic acid was transformed into (1S,5S)-(-)-5-(hydroxymethyl) -2-cyclohexen-1-ol via iodolactonization, subsequent elimination of iodine with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and reduction with lithium aluminum hydride (LAH).
Catalytic sp3–sp3Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules
Abdulla, Othman,Clayton, Adam D.,Faulkner, Robert A.,Gill, Duncan M.,Rice, Craig R.,Walton, Scarlett M.,Sweeney, Joseph B.
supporting information, p. 1494 - 1497 (2017/02/10)
A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.
A-ring hydroxymethyl 19-nor analogs of the natural hormone 1α,25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation
Hatcher, Mark A.,Peleg, Sara,Dolan, Patrick,Kensler, Thomas W.,Sarjeant, Amy,Posner, Gary H.
, p. 3964 - 3976 (2007/10/03)
A series 5-8 of 1- and 3-CH2OH 19-nor analogs of the hormone calcitriol (1) has been prepared. Surprisingly, 19-nor 1α-CH2OH analog 5a is more antiproliferative at 100 nM concentration than the corresponding regioisomeric analog 6a w