Stereocontrolled Synthesis of (-)-Bactobolin A

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F20%3A00114438" target="_blank" >RIV/00216224:14310/20:00114438 - isvavai.cz</a>
Alternative codes found
RIV/00159816:_____/20:00072975
Result on the web
<a href="https://doi.org/10.1021/jacs.0c01554" target="_blank" >https://doi.org/10.1021/jacs.0c01554</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jacs.0c01554" target="_blank" >10.1021/jacs.0c01554</a>

Result language
angličtina
Original language name
Stereocontrolled Synthesis of (-)-Bactobolin A
Original language 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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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