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The Complete Structure of Maitotoxin, Part II: Configuration of the C135C142 Side Chain and Absolute Configuration of the Entire Molecule
Author(s) -
omura Taro,
Sasaki Makoto,
Matsumori Nobuaki,
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.199616751
Subject(s) - stereocenter , absolute configuration , side chain , natural product , chemistry , stereochemistry , molecule , organic chemistry , enantioselective synthesis , polymer , 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.