Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A

We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck a...

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Detalles Bibliográficos
Autores principales: Zhang, Tingrong, Miao, Shaojie, Zhang, Mingxiao, Liu, Wenjie, Wang, Liang, Chen, Yue
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8066987/
https://www.ncbi.nlm.nih.gov/pubmed/33807472
http://dx.doi.org/10.3390/md19040198
Descripción
Sumario:We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck asymmetric vinylogous aldol reaction was employed to improve this transformation.

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