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The Complete Structure of Maitotoxin, Part I: Configuration of the C1C14 Side Chain
Author(s) -
Sasaki Makoto,
Matsumori Nobuaki,
Maruyama Takahiro,
omura Taro,
Murata Michio,
Tachibana Kazuo,
Yasumoto Takeshi
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199616721
Subject(s) - stereocenter , side chain , natural product , chemistry , stereochemistry , absolute configuration , product (mathematics) , chain (unit) , organic chemistry , enantioselective synthesis , physics , mathematics , polymer , astronomy , geometry , catalysis
All's well that ends well! The complete assignment of the structure of the largest known natural product that is not a biopolymer (maitotoxin) has concluded with the determination of the configurations of the stereogenic centers in its two acyclic side chains. The results of NMR studies were confirmed by comparison with synthesized model compounds. The absolute configuration was determined by analysis of a fragment of the natural product and a corresponding synthesized unit by GC with a chiral column. In the contracted structure below, the acyclic side chains are attached to the termini of a polycyclic polyether.