Synthesis of 2,5-dialkyl-substituted tetrahydrofurans — symmetrical analogs of natural acetogenins

Synthesis of 2,5-dialkyl-substituted tetrahydrofurans — symmetrical analogs of natural acetogenins Full article

Journal

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

Output data

Year: 2023, Volume: 72, Number: 3, Pages: 689-696 Pages count : 8 DOI: 10.1007/s11172-023-3833-6

Authors

Makarov A.A. ¹ , Ishbulatov I.V. ¹ , Makarova E.Kh. ¹ , Dzhemilev U.M. ² , D’yakonov V.A. 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, Russian Academy of Sciences, Moscow, Russian Federation

An efficient method has been developed for the synthesis of 2,5-dialkyl-substituted tetrahydrofurans, analogues of natural acetogenins. A series of tetrahydrofurans of this type have been obtained using the Ti-catalyzed homo-cyclomagnesiation of terminal 1,2-dienes at the key stage. By Ru-catalyzed oxidation of symmetrical nZ,(n+4)Z—dienes, ketols containing a tetrahydrofuran fragment were synthesized. Diastereoselective reduction of the carbonyl group of these ketols with L-selectride leads to diols, whereas oxidation of their hydroxyl groups with the Dess—Martin periodinane results in the formation of previously unreported diketones in quantitative yields.

Makarov A.A. , Ishbulatov I.V. , Makarova E.K. , Dzhemilev U.M. , D’yakonov V.A.
Synthesis of 2,5-dialkyl-substituted tetrahydrofurans — symmetrical analogs of natural acetogenins
Russian Chemical Bulletin. 2023. V.72. N3. P.689-696. DOI: 10.1007/s11172-023-3833-6 WOS Scopus OpenAlex

Web of science:	WOS:001031662300011
Scopus:	2-s2.0-85153275325
OpenAlex:	W4365814941

DB	Citing
OpenAlex	8
Scopus	7
Web of science	7