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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - 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

Project

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Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2020

Confidentiality

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

Name of the periodical

Tetrahedron

ISSN

0040-4020

e-ISSN

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Volume of the periodical

76

Issue of the periodical within the volume

15

Country of publishing house

GB - UNITED KINGDOM

Number of pages

13

Pages from-to

"Article Number: 131111"

UT code for WoS article

000525714700014

EID of the result in the Scopus database

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