Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F21%3A10438546" target="_blank" >RIV/00216208:11160/21:10438546 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=1W0vecEm9X" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=1W0vecEm9X</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3762/bjoc.17.188" target="_blank" >10.3762/bjoc.17.188</a>
Alternative languages
Result language
angličtina
Original language name
Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation
Original language description
A new highly diastereoselective synthesis of the polyhydroxylated pyrrolidine alkaloid (+/-)-codonopsinol B and its N-nor-methyl analogue, starting from achiral materials, is presented. The strategy relies on the trans-stereoselective epoxidation of 2,3-dihydroisoxazole with in situ-generated DMDO, the syn-selective alpha-chelation-controlled addition of vinyl-MgBr/CeCl3 to the isoxazolidine-4,5-diol intermediate, and the substrate-directed epoxidation of the terminal double bond of the corresponding gamma-amino-alpha,beta-diol with aqueous hydrogen peroxide catalyzed by phosphotungstic heteropoly acid. Each of the key reactions proceeded with an excellent diastereoselectivity (dr > 95:5). (+/-)-Codonopsinol B was prepared in 10 steps with overall 8.4% yield. The antiproliferative effect of (+/-)-codonopsinol B and its N-nor-methyl analogue was evaluated using several cell line models.
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
30104 - Pharmacology and pharmacy
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Beilstein Journal of Organic Chemistry
ISSN
1860-5397
e-ISSN
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Volume of the periodical
17
Issue of the periodical within the volume
November
Country of publishing house
DE - GERMANY
Number of pages
6
Pages from-to
2781-2786
UT code for WoS article
000722951500001
EID of the result in the Scopus database
2-s2.0-85122371537