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Synthesis of an Advanced Model of Zetekitoxin AB Focusing on the N ‐Acylisoxazolidine Amide Structure Corresponding to C13–C17
Author(s) -
Nishikawa Toru,
Wang Chao,
Akimoto Takafumi,
Koshino Hiroyuki,
Nagasawa Kazuo
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402206
Subject(s) - moiety , chemistry , amide , stereochemistry , intramolecular force , saxitoxin , lactam , combinatorial chemistry , natural product , total synthesis , organic chemistry , toxin , biochemistry
Abstract Zetekitoxin AB (ZTX) is a neurotoxin bearing a saxitoxin core structure together with a characteristic nine‐membered macrocyclic lactam involving a N ‐acylisoxazolidine moiety and a N ‐hydroxylcarbonylmethyl group. We describe a synthesis of an advanced model for ZTX bearing saxitoxin core structure with N ‐acylisoxazolidine moiety, i.e., C13–C17. In this synthesis, the isoxazolidine amide moiety of a ZTX analogue was constructed by reaction of an isoxazolidine with the carboxylic acid at C13 of STX, which was obtained by oxidation of the axially oriented alcohol at C13 2‐azaadamantane N ‐oxyl (AZADO) in the presence of NaClO and NaClO 2 . The 13 C NMR signal of C13 in the resulting ZTX analogue was discussed by comparison with the reported spectral data for natural product of ZTX.