Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety

Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 6, Pages: 1623-1630 Pages count : 8 DOI: 10.1007/s11172-024-4278-7

Authors

Islamov I.I. ¹ , Gaisin I.V. ¹ , Dzhemilev U.M. ² , D’yakonov V.A. ²

Affiliations

1	Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Bashkortostan, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A stereoselective synthesis of new (6Z,10Z)-16-hydroxyhexadeca-6,10-dienoic and (7Z,11Z)-18-hydroxyoctadeca-7,11-dienoic acid that involved the Ti-catalyzed homocyclomagnesiation of the functionally substituted 1,2-dienes was developed. Subsequent intramolecular cyclization of the synthesized ω-hydroxyalkadienoic acids in the presence of catalytic amounts (2.5–10 mol.%) of hafnium(iv) triflate gave unsaturated macrocyclic lactones and diolides with pharmacophoric 1Z,5Z-diene moieties.

Islamov I.I. , Gaisin I.V. , Dzhemilev U.M. , D’yakonov V.A.
Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety
Russian Chemical Bulletin. 2024. V.73. N6. P.1623-1630. DOI: 10.1007/s11172-024-4278-7 WOS Scopus OpenAlex

Web of science:	WOS:001280216600024
Scopus:	2-s2.0-85199774522
OpenAlex:	W4401012058

DB	Citing
OpenAlex	5
Scopus	3
Web of science	3