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1.
J Org Chem ; 87(2): 1325-1334, 2022 01 21.
Artigo em Inglês | MEDLINE | ID: mdl-35007075

RESUMO

An asymmetric synthetic route to (-)-galanthamine (1), a pharmacologically active Amaryllidaceae alkaloid used for the symptomatic treatment of early onset Alzheimer's disease, was successfully established with very high levels of stereocontrol. The key to achieving high chemo- and stereo-selectivity in this approach was the use of transition-metal-mediated reactions, namely, enyne ring-closing metathesis, Heck coupling, and titanium-based asymmetric allylation.


Assuntos
Alcaloides , Doença de Alzheimer , Galantamina , Humanos
2.
Org Lett ; 10(12): 2489-92, 2008 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-18489103

RESUMO

An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP 4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.


Assuntos
Furanos/química , Furanos/síntese química , Polienos/química , 4-Butirolactona/química , Alquilação , Ciclização , Furanos/farmacologia , Estrutura Molecular , Plantas Medicinais/química , Rollinia/química , Estereoisomerismo
3.
Org Lett ; 9(10): 1867-9, 2007 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-17429978

RESUMO

An enantioselective synthesis of (-)-galanthamine has been realized in 11 linear steps starting from isovanillin. A Mitsunobu aryl ether forming reaction was used to assemble the galanthamine backbone, which was stitched together using enyne ring-closing metathesis, Heck, and N-alkylation reactions affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically enriched propargylic alcohol 13.


Assuntos
Galantamina/síntese química , Ciclização , Galantamina/química , Estrutura Molecular , Estereoisomerismo
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