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Stereochemical Studies on Sphinxolide: Advances in the J ‐Based NMR Determination of the Relative Configuration of Flexible Systems
Author(s) -
Bassarello Carla,
Bifulco Giuseppe,
Zampella Angela,
D’Auria Maria Valeria,
Riccio Raffaele,
GomezPaloma Luigi
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:1<39::aid-ejoc39>3.0.co;2-9
Subject(s) - chemistry , heteronuclear single quantum coherence spectroscopy , chemical shift , nmr spectra database , stereochemistry , molecule , proton nmr , two dimensional nuclear magnetic resonance spectroscopy , nuclear magnetic resonance spectroscopy , combinatorial chemistry , computational chemistry , spectral line , organic chemistry , physics , astronomy
An improved version of the J ‐based NMR configurational analysis of flexible organic molecules, that relies on extensive use of HSQC‐TOCSY spectra, was applied to the stereochemical study of sphinxolide, a potent anti‐tumor marine macrolide acting on cell microfilaments that has lately proven to circumvent multi‐drug‐resistance (MDR) in cancer cells. NMR data allowed stereochemical assignment of all molecular segments except the C18−C19 unit, whose configuration had to be addressed by a chemical/degradative approach.