823-36-9Relevant articles and documents
Highly Enantioselective, Organocatalytic, and Scalable Synthesis of a Rare cis,cis-Tricyclic Diterpenoid
Townsend, Daniel,Shankland, Kenneth,Weymouth-Wilson, Alex,Komsta, Zofia,Evans, Tim,Cobb, Alexander J. A.
supporting information, p. 3504 - 3508 (2020/03/05)
A highly enantioselective, organocatalytic, and scalable synthesis of a very unusual cis-decalin-cis-hydrindane tricyclic diterpenoid system has been achieved. Despite the prevalent pharmacological space that the related trans,trans and trans,cis-systems occupy, there have been no reports of an asymmetric synthesis of the cis,cis systems in the literature until now. We demonstrate the flexibility of our approach not only through access to a diverse range of products, all of which are attained in exceptionally high selectivities, but also by showing their easy conversion to the corresponding trans,cis-system and other derivatives.
Direct amino acid-catalyzed cascade biomimetic reductive alkylations: Application to the asymmetric synthesis of Hajos-Parrish ketone analogues
Ramachary, Dhevalapally B.,Kishor, Mamillapalli
supporting information; experimental part, p. 4176 - 4187 (2009/02/07)
A direct amino acid-catalyzed chemo- and enantioselective process for the double cascade synthesis of highly substituted 2-alkyl-cyclopentane-1,3-diones, 2-alkyl-3-methoxy-cyclopent-2-enones and Hajos-Parrish (H-P) ketone analogs is presented via reductive alkylation chemistry. For the first time, we have developed a single-step alkylation of cyclopentane-1,3-dione with aldehydes/ketones and a Hantzsch ester through an organocatalytic reductive alkylation strategy. A direct combination of amino acid-catalyzed cascade olefination-hydrogenation and cascade Robinson annulations of cyclopentane-1,3-dione, aldehydes/ketones, a Hantzsch ester and methyl vinyl ketone furnished the highly functionalized H-P ketone analogues in good to high yields and with excellent enantioselectivities. Many of the reductive alkylation products have shown direct applications in pharmaceutical chemistry.
Selective reduction of the acyl group in cyclic α-acyl-β-dicarbonyl compounds with sodium cyanoborohydride. Efficient synthesis of cyclic α-alkyl-β-dicarbonyl compounds
Pashkovsky,Lokot',Lakhvich
, p. 324 - 326 (2007/10/03)
Efficient synthesis of cyclic α-alkyl-β-dicarbonyl compounds of the cyclopentane, cyclohexane, tetronic acid, and α-pyrone series from the corresponding cyclic α-acyl-β-dicarbonyl compounds under the action of NaBH3(CN) in a THF-HCl system is described.
