Complete Relative Stereochemistry of Maitotoxin

Autor:	Jiang-Ping Wu, Hitoshi Oinuma, John A. DeMattei, Yoshito Kishi, Wanjun Zheng, Laura R. Cook, Jingwu Duan
Rok vydání:	1996
Předmět:	Maitotoxin chemistry.chemical_compound Colloid and Surface Chemistry Proton Stereochemistry Chemistry Diastereomer Organic synthesis General Chemistry Carbon-13 NMR Biochemistry Catalysis
Zdroj:	Journal of the American Chemical Society. 118:7946-7968
ISSN:	1520-5126 0002-7863
Popis:	By addressing the relative stereochemistry of the four acyclic portions via organic synthesis, the complete relative stereochemistry of maitotoxin (MTX) has been established as 1B. The relative stereochemistry of the C.1−C.15 portion was elucidated via a two-phase approach: (1) the synthesis of the eight diastereomers possible for model C, representing the C.1−C.11 portion, and the eight diastereomers possible for model D, representing the C.11−C.15 portion, and the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 9 and 35 represent the relative stereochemistry of the corresponding portions of MTX; (2) the synthesis of the two remote diastereomers 51 and 52, and comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 51 represents the relative stereochemistry of the C.1−C.15 portion of MTX. The relative stereochemistry of the C.35−C.39, C.63−C.68, and C.134−C.142 acyclic portions was established via (1) the synthesis of the ...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c8be507c68a0c4541f7d3d8f6f1168ca https://doi.org/10.1021/ja961230+ Zobrazit plný text záznamu