61586-79-6Relevant articles and documents
A Formal Synthesis of Ptaquilosin. The Aglycon of a Potent Bracken Carcinogen Ptaquiloside
Cossy, Janine,Ibhi, Said,Kahn, Philippe H.,Tacchini, Laura
, p. 7877 - 7880 (1995)
A formal synthesis of racemic and optically active ptaquilosin has been achieved from the commercially available methyl 2-oxocyclopentanecarboxylate.
Is the ring conformation the most critical parameter in lipase-catalysed acylation of cycloalkanols?
Levy, Laura M.,Lavandera, Ivan,Gotor, Vicente
, p. 2572 - 2577 (2004)
CAL-B catalysed the resolution of several five and six-membered cyclic β-hydroxy esters efficiently with the exception of the cis-cyclohexanol (±)-4. When employing molecular modelling techniques the conformation turned out to be the most important determ
Chemo-enzymatic synthesis of (R)-5-hydroxymethyl-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethylsulfonate, a potential chiral building block for multicyclic terpenoids
Kuwata, Kazuaki,Hanaya, Kengo,Sugai, Takeshi,Shoji, Mitsuru
, p. 964 - 968 (2017/07/11)
The chemo-enzymatic synthesis of (R)-5-hydroxymethyl-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethylsulfonate, a potential chiral building block for polycyclic terpenoids containing a five–membered ring having isopropyl and angular methyl substituents, such as erinacin A and dolatriol, was achieved over 11 steps from ethyl 2-oxocyclopentane-1-carboxylate. The key synthetic precursor for this triflate was ethyl (1S,2R)-2-hydroxycyclopentanecarboxylate (>99% ee), which was prepared by a lipase-catalyzed enantioselective hydrolysis of the corresponding racemic acetate. The antipodal (S)-triflate is expected to be the synthetic intermediate for another group of terpenoids involving hamigeran B and stolonidiol. Enantiomerically pure (1R,2S)-hydroxyester (>99% ee) was prepared in high yield using the asymmetric reduction of the oxoester with commercially available carbonyl reductase, “Chiralscreen OH”-E001.
The fluoroalkene motif as a surrogate of the amide bond: Syntheses of AA-Ψ[(Z) and (E)-CFCH]-Pro pseudodipeptides and an Enalapril analogue
Villiers, Emilie,Couve-Bonnaire, Samuel,Cahard, Dominique,Pannecoucke, Xavier
, p. 7054 - 7062 (2015/08/19)
This work describes the optimization process for the synthesis of pseudodipeptides featuring a proline bound to another amino acid through a fluoroalkene moiety that act as an amide bond surrogate. The synthetic methodology is extended to non-peptidic molecules as demonstrated in the design and synthesis of an Enalapril analogue.
