Autoren:	Trippe, Lukas Nava, Analuisa Frank, Andrea Nubbemeyer, Udo
Titel:	Synthesis of enantiopure 6,11-methylene lipoxin B4 methyl ester
Online-Publikationsdatum:	26-Apr-2022
Erscheinungsdatum:	2021
Sprache des Dokuments:	Englisch
Zusammenfassung/Abstract:	The synthesis of Lipoxin B4 analogs (LXB4) to gain access to stabilized inflammation resolving compounds is an actual field of research. Focusing on variation and stabilization of the conjugated E,Z,E,E C6–C13 tetraene moiety of natural LXB4, a methylene bridge introduced between C6 and C11 suppresses any Z/E isomerization of the C8–C9 olefin. Intending to enable prospective structure variations in connection with the C1–C5 and C14–C20 fragments, a convergent total synthesis has been developed. Optically active C1–C12 building blocks were build-up from cycloheptatriene 1-carbonester (C6–C11, C21) and glutaryl chloride (C1–C5) using Friedel-Crafts-type acylation and chiral HPLC. The C13–C20 segment had been generated via a five-step sequence starting from heptanoyl chloride. Horner key olefination enabled the assembly of the carbon backbone. A final five-step sequence including a chelate Cram reduction of the unsaturated ketone moiety afforded the target 6,11-methylene LXB4 methyl ester.
DDC-Sachgruppe:	540 Chemie 540 Chemistry and allied sciences
Veröffentlichende Institution:	Johannes Gutenberg-Universität Mainz
Organisationseinheit:	FB 09 Chemie, Pharmazie u. Geowissensch.
Veröffentlichungsort:	Mainz
ROR:	https://ror.org/023b0x485
DOI:	http://doi.org/10.25358/openscience-6907
Version:	Published version
Publikationstyp:	Zeitschriftenaufsatz
Nutzungsrechte:	CC BY
Informationen zu den Nutzungsrechten:	https://creativecommons.org/licenses/by/4.0/
Zeitschrift:	European journal of organic chemistry 2021 7
Seitenzahl oder Artikelnummer:	1156 1167
Verlag:	Wiley-VCH
Verlagsort:	Weinheim
Erscheinungsdatum:	2021
ISSN:	1099-0690
DOI der Originalveröffentlichung:	10.1002/ejoc.202001591
Enthalten in den Sammlungen:	JGU-Publikationen