169170-72-3Relevant academic research and scientific papers
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
Chen, Violet Yijang,Kwon, Ohyun
, p. 8874 - 8881 (2021/03/17)
Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
Anionic cyclizations of pentynones and hexynones: Access to furan and pyran derivatives
Nicola, Thomas,Vieser, Ralf,Eberbach, Wolfgang
, p. 527 - 538 (2007/10/03)
On treatment with base the pentynones 8a-f undergo anionic addition reactions of the resulting enolate species to the alkyne moiety and afford the 2,5-disubstituted furans 10a-f in yields ranging from 10-91%. The proposed mechanism involves the 2-methylen
STUDIES ON THE SYNTHESIS OF FURANS BY ANIONIC CYCLIZATION OF 4-PENTYNONES
Vieser, Ralf,Eberbach, Wolfgang
, p. 4405 - 4408 (2007/10/02)
The synthesis of 5-substituted 2-carbomethoxymethyl-furans 4 is achieved by base promoted cyclization of the 4-pentynones 3a-e which are easily accessible from the 4-pentynal 1.
