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An isolable acyclic hemiacetal of ansamitocin P‐3
Author(s) -
Segraves Nathaniel L.,
Yazzie Derrick,
Deese Alan J.
Publication year - 2012
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2876
Subject(s) - hemiacetal , chemistry , acetal , intramolecular force , stereochemistry
During impurity analysis of maytansinol (2), produced from the reduction of ansamitocin P‐3 (AP‐3, 1), a surprisingly stable acyclic hemiacetal (4) was isolated. A combination of 1D and 2D NMR experiments, along with liquid chromatography–mass spectrometry data was used to confirm the structure. Comparison of NMR data to the previously reported bridged acetal (3), a by‐product of AP‐3 reduction, supports reassignment of the latter to the former. Additionally, ROESY data, in conjunction with minimum energy calculations, support intramolecular hydrogen bonding that is involved in stabilizing the hemiacetal. This report adds another example to the very short list of isolable acyclic hemiacetals. Copyright © 2012 John Wiley & Sons, Ltd.