Enantioselective Catalytic Crotylboration Based Syntheses of the C(7)-C(18(20)) Fragments of Polyketides Isolated from Streptomyces gramineus
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F21%3A10471458" target="_blank" >RIV/00216208:11310/21:10471458 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=J7l72XVLwt" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=J7l72XVLwt</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/hlca.202100170" target="_blank" >10.1002/hlca.202100170</a>
Alternative languages
Result language
angličtina
Original language name
Enantioselective Catalytic Crotylboration Based Syntheses of the C(7)-C(18(20)) Fragments of Polyketides Isolated from Streptomyces gramineus
Original language description
A general modular enantioselective synthetic approach to the C(7)-C(18) and the C(7)-C(20) fragment belonging to E-492, actinofuranone A, and JBIR-108 was developed. The crucial synthetic step relies on highly enantioselective crotylboration of aldehydes catalyzed by a chiral TRIP PA giving rise to highly enantioenriched terminal alkenes (86 and 88 % ee on the preparative scale). The alkenes were subsequently converted into the title products. Further important synthetic steps included Ru-catalyzed alkene cross-metathesis and Suzuki coupling reactions. The approach consists of five synthetic steps starting from easily available aldehydes and other reaction partners.
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
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA21-29124S" target="_blank" >GA21-29124S: REAP and Other Catalytic Reactions in Synthesis of Nitrogen-Embbeded Polyaromatic Hydrocarbons</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
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
Helvetica Chimica Acta
ISSN
0018-019X
e-ISSN
1522-2675
Volume of the periodical
104
Issue of the periodical within the volume
12
Country of publishing house
CH - SWITZERLAND
Number of pages
10
Pages from-to
e2100170
UT code for WoS article
000708104800001
EID of the result in the Scopus database
2-s2.0-85117177631