Stereocontrolled Synthesis of (-)-Bactobolin A

J 2020

Stereocontrolled Synthesis of (-)-Bactobolin A

VOJÁČKOVÁ, Petra, Lucyna MICHALSKA, Marek NEČAS, Dimitri SHCHERBAKOV, Erik C. BÖTTGER et. al.

Basic information

Original name

Stereocontrolled Synthesis of (-)-Bactobolin A

Authors

VOJÁČKOVÁ, Petra (203 Czech Republic, belonging to the institution), Lucyna MICHALSKA (616 Poland, belonging to the institution), Marek NEČAS (203 Czech Republic, belonging to the institution), Dimitri SHCHERBAKOV, Erik C. BÖTTGER, Jiří ŠPONER (203 Czech Republic), Judit E. ŠPONER and Jakub ŠVENDA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of the American Chemical Society, Washington, American Chemical Society, 2020, 0002-7863

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 15.419

RIV identification code

RIV/00216224:14310/20:00114438

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/jacs.0c01554

UT WoS

000529156100012

Keywords in English

Organic compounds; Anions; Organic reactions; Aldol reactions; Stereoselectivity

Abstract

V originále

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.

Links

EF16_025/0007381, research and development project

Name: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou

GA20-11898S, research and development project

Name: Syntéza a biologické testování analogů přírodních antibiotik bactobolinů

Investor: Czech Science Foundation

LM2015043, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

LM2015063, research and development project

Name: Národní infrastruktura chemické biologie (Acronym: CZ-OPENSCREEN)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

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.

@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.

Detailed Information on Publication Record