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Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry

Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC(50) 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In th...

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Detalles Bibliográficos
Autores principales: Shi, Hao-yun, Xie, Yang, Hu, Pei, Guo, Zi-qiong, Lu, Yi-hong, Gao, Yu, Huang, Cheng-gang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6266257/
https://www.ncbi.nlm.nih.gov/pubmed/30380702
http://dx.doi.org/10.3390/md16110414
Descripción
Sumario:Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC(50) 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia–Kocienski olefination as the key steps. Comparison of (13)C NMR spectra revealed the relative structure of fragment C15–C32 of alotamide.