39007-93-7Relevant academic research and scientific papers
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
Chen, Violet Yijang,Kwon, Ohyun
supporting information, 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.
Illustrating the power of singlet oxygen chemistry in a synthetic context: Biomimetic syntheses of litseaverticillols A-G, I and J and the structural reassignment of litseaverticillol E
Vassilikogiannakis, Georgios,Margaros, Ioannis,Montagnon, Tamsyn,Stratakis, Manolis
, p. 5899 - 5907 (2007/10/03)
Biomimetic syntheses of the litseaverticillols A-G, I and J are reported herein. The syntheses rely heavily on the application of two different modes of reaction for photochemically generated singlet oxygen, namely, the [4+2] cycloaddition of singlet oxygen (1O2) with furans and the ene reaction of 1O2 with double bonds. The highlight of these syntheses is a one-pot cascade sequence, involving five synthetic operations initiated by a [4+2] reaction, to form the fully functionalised litseaverticillol core. A series of regioselective ene reactions are then used to appositely functionalise the side chains. The synthesis of litseaverticillol E (both its originally proposed and its actual structures) allows a structural reassignment of this natural product.
Biomimetic Total Synthesis of Litseaverticillols A, C, D, F, and G: Singlet-Oxygen-Initiated Cascades
Vassilikogiannakis, Georgios,Stratakis, Manolis
, p. 5465 - 5468 (2007/10/03)
Natural weapons against HIV, litseaverticillols A (2) and C, have been synthesized from sesquirosefuran (1) by a rapid and efficient biomimetic total synthesis involving a chemo- and stereoselective singlet-oxygen-initiated tandem sequence (see scheme). Litseaverticillols D, F, and G were readily synthesized from litseaverticillol A through a regioselective 1O 2 ene reaction.
Selective Alkylation and Allylation of Allylic Halides by Tetraorganoidates: Regio- and Stereo-selective Synthesis of Rosefuran and Sesquirosefuran
Araki, Shuki,Jin, Shun-Ji,Butsugan, Yasuo
, p. 549 - 552 (2007/10/02)
Tetraalkylindanes regioselectively alkylate allylic bromides at the α-carbon.In this way, 1,5-dienes have been regio- and stereo-selectively synthesized by the allyl-allyl coupling of allylic bromides and allylic indates, including rosefuran 1 and sequirosefuran 3.
REGIO-CONTROLLED PRENYLATION AND GERANYLATION OF 3-FURYLMETHYLMAGNESIUM BROMIDE. SELECTIVE SYNTHESES OF 3-SUBSTITUTED FURANOID AND 2-SUBSTITUTED 3-METHYLFURANOID TERPENES.
Araki,Butsugan
, p. 1446 - 1449 (2007/10/02)
Coupling reactions of 3-furylmethylmagnesium bromide with prenyl and geranyl diethyl phosphates gave 2-substituted 3-methylfurans, rosefuran and sesquirosefuran, as the main products. When the reactions were carried out in the presence of a catalytic amount of copper(I) iodide, normal coupling occurred and 3-substituted furans, perillene and dendrolasin, were formed in good yields. The related naturally occurring 3-substituted thiophene, 3-(4-methyl-3-pentenyl)thiophene, was also synthesized from 3-thienylmethylmagnesium bromide and prenyl diethy phosphate.
SELECTIVE SYNTHESES OF DENDROLASIN AND SESQUIROSEFURAN BY THE COUPLING OF 3-FURYLMETHYLMAGNESIUM BROMIDE WITH GERANYL DIETHYL PHOSPHATE
Araki, Shuki,Butsugan, Yasuo
, p. 177 - 178 (2007/10/02)
Coupling reaction of 3-furylmethylmagnesium bromide with geranyl diethyl phosphate in the presence and the absence of copper(I) iodide affords dendrolasin and sesquirosefuran, respectively, in ca. 80 percent selectivity
A SIMPLE ROUTE TO FURANS BY ORGANOALUMINUM REAGENTS
Ishiguro, Masaharu,Ikeda, Nobuo,Yamamoto, Hisashi
, p. 1029 - 1030 (2007/10/02)
2,3-Disubstituted furans are synthesized from the reaction of aldehydes with allenylaluminum reagents derived from propargylic ethers.
A FACILE SYNTHESIS OF 4-PHENYLTHIO-2(5H)-FURANONE DERIVATIVES. SYNTHESIS OF SESQUIROSE FURAN AND BULLATENONE
Takahashi, Yasuhiro,Hagiwara, Hisahiro,Uda, Hisashi,Kosugi, Hiroshi
, p. 225 - 229 (2007/10/02)
Condensation of the dianions derived from E-3-(phenylthio)prop-2-enoic acid and its 2-methyl homologue with aldehydes and ketones provides a facile one step synthesis of 5-substituted 4-phenylthio-2(5H)-furanone derivatives.The application to the synthesi
