Stereocontrolled Synthesis of (-)-Bactobolin A
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F20%3A00524322" target="_blank" >RIV/68081707:_____/20:00524322 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/jacs.0c01554" target="_blank" >https://pubs.acs.org/doi/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>
Alternative languages
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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Classification
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
10608 - Biochemistry and molecular biology
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN
1520-5126
e-ISSN
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Volume of the periodical
142
Issue of the periodical within the volume
16
Country of publishing house
US - UNITED STATES
Number of pages
6
Pages from-to
7306-7311
UT code for WoS article
000529156100012
EID of the result in the Scopus database
2-s2.0-85085014880