Asymmetric Synthesis of Diastereomeric Diaminoheptanetetraols. A Proposal for the Configuration of (+)-Zwittermicin A
- 11 January 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (3) , 437-440
- https://doi.org/10.1021/ol062804a
Abstract
A proposed absolute configuration for the 7 stereocenters in (+)-zwittermicin A is described based on asymmetric synthesis of six diastereomeric 2,6-diamino-1,3,5,7-heptanetetraols corresponding to the C9−C15 segment, pairwise 13C NMR chemical shift difference analysis of the models with the natural product, interpretation of enantiospecificity of the serine loading domain of the zwittermicin A biosynthetic gene cluster, and degradation of the natural product.Keywords
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