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Stereocontrolled Synthesis of (-)-Bactobolin A

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

Rok publikování 2020
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of the American Chemical Society
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www https://doi.org/10.1021/jacs.0c01554
Doi http://dx.doi.org/10.1021/jacs.0c01554
Klíčová slova Organic compounds; Anions; Organic reactions; Aldol reactions; Stereoselectivity
Popis 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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