Issue 9, 2014

Enantioselective Pd-catalyzed tandem allylic alkylation reaction using monodentate phosphoramidite ligands for the formal total synthesis of huperzine A

Abstract

A small library of fine-tunable monodentate phosphoramidite (MPN) ligands was found useful in selecting a highly efficient chiral ligand for the enantioselective Pd-catalyzed tandem allylic alkylation reaction. The reaction gave a critical tricyclic key intermediate with high enantiopurity for the formal total synthesis of (−)-huperzine A, a Lycopodium alkaloid derived from the club moss Huperzia serrata that possesses potent inhibitory activity against acetylcholine esterase (ACHe).

Graphical abstract: Enantioselective Pd-catalyzed tandem allylic alkylation reaction using monodentate phosphoramidite ligands for the formal total synthesis of huperzine A

Supplementary files

Article information

Article type
Research Article
Submitted
28 Чер 2014
Accepted
19 Сер 2014
First published
20 Сер 2014

Org. Chem. Front., 2014,1, 1062-1066

Author version available

Enantioselective Pd-catalyzed tandem allylic alkylation reaction using monodentate phosphoramidite ligands for the formal total synthesis of huperzine A

C. Lin, C. Chien and I. Ojima, Org. Chem. Front., 2014, 1, 1062 DOI: 10.1039/C4QO00180J

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