Synthesis of aryl-substituted derivatives of acetogenins using the Ti-catalyzed homo-cyclomagnesiation of 1,2-dienes as a key step

Synthesis of aryl-substituted derivatives of acetogenins using the Ti-catalyzed homo-cyclomagnesiation of 1,2-dienes as a key step Full article

Journal

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

Output data

Year: 2023, Volume: 72, Number: 10, Pages: 2366-2371 Pages count : 6 DOI: 10.1007/s11172-023-4034-4

Authors

Makarov A.A. ¹ , Ishbulatov I.V. ¹ , Makarova E.Kh. ¹ , D’yakonov V.A. ² , Dzhemilev U.M. ²

Affiliations

1	Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences, Moscow, Russian Federation

New symmetric aryl-substituted derivatives of acetogenins were synthesized using the Ti-catalyzed homo-cyclomagnesiation of aryl-substituted 1,2-dienes at the key step. Ruthenium catalyzed oxidative cyclization of symmetric aryl-substituted 1Z,5Z-dienes was used to synthesize diols and ketols containing a tetrahydrofuran fragment. Diastereoselective reduction of ketols with L-selectride yielded target diols. In addition, by oxidation of ketols with Dess—Martin periodinane, diketones were synthesized in high yields.

Makarov A.A. , Ishbulatov I.V. , Makarova E.K. , D’yakonov V.A. , Dzhemilev U.M.
Synthesis of aryl-substituted derivatives of acetogenins using the Ti-catalyzed homo-cyclomagnesiation of 1,2-dienes as a key step
Russian Chemical Bulletin. 2023. V.72. N10. P.2366-2371. DOI: 10.1007/s11172-023-4034-4 WOS Scopus OpenAlex

Web of science:	WOS:001103056900009
Scopus:	2-s2.0-85176147351
OpenAlex:	W4388594313

DB	Citing
OpenAlex	5
Scopus	5
Web of science	5