Publication details

Stereocontrolled Synthesis of (-)-Bactobolin A

Authors

VOJÁČKOVÁ Petra MICHALSKA Lucyna NEČAS Marek SHCHERBAKOV Dimitri BÖTTGER Erik C. ŠPONER Jiří ŠPONER Judit E. ŠVENDA Jakub

Year of publication 2020
Type Article in Periodical
Magazine / Source Journal of the American Chemical Society
MU Faculty or unit

Faculty of Science

Citation
Web https://doi.org/10.1021/jacs.0c01554
Doi http://dx.doi.org/10.1021/jacs.0c01554
Keywords Organic compounds; Anions; Organic reactions; Aldol reactions; Stereoselectivity
Description A stereoselective synthesis of the ribosome-binding antitumor antibiotic (-)-bactobolin A is reported. The presented approach makes effective use of (-)-quinic acid as a chiral pool starting material and substrate stereocontrol to establish the five contiguous stereocenters of (-)-bactobolin A. The key steps of the synthesis include a stereoselective vinylogous aldol reaction to introduce the unusual dichloromethyl substituent, a completely diastereoselective rhodium(II)-catalyzed C-H amination reaction to set the configuration of the axial amine, and an intramolecular alkoxycarbonylation to build the bicyclic lactone framework. The developed synthetic route was used to prepare 90 mg of (-)-bactobolin A trifluoroacetate in 10% overall yield.
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