Angewandte Chemie International Edition
10.1002/anie.202108157
COMMUNICATION
reaction. An orange-colored side product was isolated in 21%
yield, which was tentatively assigned as the product of oxidative
degradation and condensation (see the SI for further details). In
the final step, the removal of the MEM protective group was
favorably performed in dichloromethane as the solvent, in which
enterocin is not soluble. The compound thus precipitated during
the deprotection reaction and could be isolated in pure form after
semi-preparative, reversed phase HPLC purification. As some
starting material was still detectable in the crude product, further
optimization of the deprotection conditions is warranted. Synthetic
enterocin (1) was shown by HPLC and NMR analysis to be, in all
scalar properties, fully identical with the natural product.[31]
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Acknowledgements
Financial support by the Deutsche Forschungsgemeinschaft (Ba
1
372/23) is gratefully acknowledged. We thank Dr. Alexander
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Keywords: aldol reaction · biomimetic synthesis · oxygenation ·
polyketides · total synthesis
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