| VOJÁČKOVÁ, Petra, Lucyna MICHALSKA, Marek NEČAS, Dimitri SHCHERBAKOV, Erik C. BÖTTGER, Jiří ŠPONER, Judit E. ŠPONER and Jakub ŠVENDA. Stereocontrolled Synthesis of (-)-Bactobolin A. Journal of the American Chemical Society. Washington: American Chemical Society, 2020, vol. 142, No 16, p. 7306-7311. ISSN 0002-7863. Available from: https://dx.doi.org/10.1021/jacs.0c01554. |
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@article{1691256,
author = {Vojáčková, Petra and Michalska, Lucyna and Nečas, Marek and Shcherbakov, Dimitri and Böttger, Erik C. and Šponer, Jiří and Šponer, Judit E. and Švenda, Jakub},
article_location = {Washington},
article_number = {16},
doi = {http://dx.doi.org/10.1021/jacs.0c01554},
keywords = {Organic compounds; Anions; Organic reactions; Aldol reactions; Stereoselectivity},
language = {eng},
issn = {0002-7863},
journal = {Journal of the American Chemical Society},
title = {Stereocontrolled Synthesis of (-)-Bactobolin A},
url = {https://doi.org/10.1021/jacs.0c01554},
volume = {142},
year = {2020}
}
TY - JOUR
ID - 1691256
AU - Vojáčková, Petra - Michalska, Lucyna - Nečas, Marek - Shcherbakov, Dimitri - Böttger, Erik C. - Šponer, Jiří - Šponer, Judit E. - Švenda, Jakub
PY - 2020
TI - Stereocontrolled Synthesis of (-)-Bactobolin A
JF - Journal of the American Chemical Society
VL - 142
IS - 16
SP - 7306-7311
EP - 7306-7311
PB - American Chemical Society
SN - 00027863
KW - Organic compounds
KW - Anions
KW - Organic reactions
KW - Aldol reactions
KW - Stereoselectivity
UR - https://doi.org/10.1021/jacs.0c01554
L2 - https://doi.org/10.1021/jacs.0c01554
N2 - 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.
ER -
VOJÁČKOVÁ, Petra, Lucyna MICHALSKA, Marek NEČAS, Dimitri SHCHERBAKOV, Erik C. BÖTTGER, Jiří ŠPONER, Judit E. ŠPONER and Jakub ŠVENDA. Stereocontrolled Synthesis of (-)-Bactobolin A. \textit{Journal of the American Chemical Society}. Washington: American Chemical Society, 2020, vol.~142, No~16, p.~7306-7311. ISSN~0002-7863. Available from: https://dx.doi.org/10.1021/jacs.0c01554.
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