A stereoselective approach in preparation of gamma-lactam precursors for oxazolomycin's synthesis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F20%3A50016708" target="_blank" >RIV/62690094:18470/20:50016708 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0040402020302325?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0040402020302325?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2020.131111" target="_blank" >10.1016/j.tet.2020.131111</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A stereoselective approach in preparation of gamma-lactam precursors for oxazolomycin's synthesis

Popis výsledku v původním jazyce

A stereoselective approach to C-3&apos; methyl attached gamma-lactam derivatives as the precursors of pyroglutamate core of oxazolomycins is described. The synthesis started from D-xylose and utilized [3,3]-heterosigmatropic rearrangement. The key lactamization was achieved with intramolecular aldol reaction and ring-closing metathesis. The accomplished stereoselective aldol cyclization was elucidated with Zimmerman-Traxler transition state models. Stereoselectivity of the aldol reaction was explained as a consequence of chelation and bridgehead atoms linkage. The present work also encompasses proposed structures of (E)- and (Z)- generated enolates during intramolecular aldol reaction. Although stereocenters were not formed during ring-closing metathesis, a stereospecific reduction of prepared double bond functionality was successfully accomplished.

Název v anglickém jazyce

A stereoselective approach in preparation of gamma-lactam precursors for oxazolomycin's synthesis

Popis výsledku anglicky

A stereoselective approach to C-3&apos; methyl attached gamma-lactam derivatives as the precursors of pyroglutamate core of oxazolomycins is described. The synthesis started from D-xylose and utilized [3,3]-heterosigmatropic rearrangement. The key lactamization was achieved with intramolecular aldol reaction and ring-closing metathesis. The accomplished stereoselective aldol cyclization was elucidated with Zimmerman-Traxler transition state models. Stereoselectivity of the aldol reaction was explained as a consequence of chelation and bridgehead atoms linkage. The present work also encompasses proposed structures of (E)- and (Z)- generated enolates during intramolecular aldol reaction. Although stereocenters were not formed during ring-closing metathesis, a stereospecific reduction of prepared double bond functionality was successfully accomplished.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Svazek periodika

76

Číslo periodika v rámci svazku

15

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

13

Strana od-do

"Article Number: 131111"

Kód UT WoS článku

000525714700014

EID výsledku v databázi Scopus

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