Asymmetric Total Synthesis of Propindilactoneâ
G, Partâ
2: Enantioselective Construction of the Fully Functionalized BCDE Ring System.
Chem Asian J
; 11(9): 1414-24, 2016 05 06.
Article
em En
| MEDLINE
| ID: mdl-26991420
ABSTRACT
The enantioselective synthesis of the fully functionalized BCDE tetracyclic ring system of propindilactoneâ
G (A) is reported. Several synthetic methods were developed and applied to achieve this goal, including 1)â
an asymmetric Diels-Alder reaction in the presence of Hayashi's catalyst for the synthesis of optically pure key intermediate 3; 2)â
an intramolecular Pauson-Khand reaction (PKR) for the stereoselective synthesis of the BCDE ring with an all-carbon chiral quaternary center at the C13 position by using the TMS-substituted acetylene as the substrate; and 3)â
Pd-catalyzed reductive hydrogenolysis for the stereoselective synthesis of the fully functionalized BCDE tetracyclic ring system. The chemistry developed herein provided a greater understanding of the total synthesis propindilactoneâ
G (A) and its analogues.
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Triterpenos
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Compostos Heterocíclicos de 4 ou mais Anéis
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article