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Studies on C(20)-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton

[Image: see text] The full details of a synthesis of the hetidine framework of the C(20)-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the na...

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Detalles Bibliográficos
Autores principales: Hamlin, Amy M., Lapointe, David, Owens, Kyle, Sarpong, Richmond
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120980/
https://www.ncbi.nlm.nih.gov/pubmed/25004408
http://dx.doi.org/10.1021/jo501214b
Descripción
Sumario:[Image: see text] The full details of a synthesis of the hetidine framework of the C(20)-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylindenes to prepare a [6–7–6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines.