76311-90-5Relevant academic research and scientific papers
The Bromination of β-Angelica Lactone Revisited: Synthesis of New 3-Bromo-5-methylene- and 3-Bromo-5-methyl-2(5H)-furanones.
Echagueen, Cristina Ochoa de,Ortuno, Rosa M.
, p. 12457 - 12462 (1994)
Several title compounds have been synthesized efficiently from β-angelica lactone by using simple and mild methods that combine bromination and dehydrobromination or debromination processes accomplished in a convenient order.
Biosynthesis of Pseudomonas-Derived Butenolides
Chowdhury, Somak,Klapper, Martin,Menzel, Klaus-Dieter,Paschold, André,Rosenbaum, Miriam A.,Schlabach, Kevin,Stallforth, Pierre,Zhang, Shuaibing
supporting information, p. 5607 - 5610 (2020/02/04)
Butenolides are well-known signaling molecules in Gram-positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram-negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagenesis, heterologous expression, and identification of key shunt and intermediate products were crucial to propose a biosynthetic pathway for both Pseudomonas-derived butenolides. Comparative transcriptomics suggests a link between styrolide formation and the regulatory networks of the bacterium.
Highly effective vinylogous Mukaiyama-Michael reaction catalyzed by silyl methide species generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane
Takahashi, Arata,Yanai, Hikaru,Zhang, Min,Sonoda, Takaaki,Mishima, Masaaki,Taguchi, Takeo
supporting information; experimental part, p. 1259 - 1265 (2010/04/29)
(Chemical Equation Presented) Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH 2CHTf2) performed as an excellent acid catalyst for the vinylogousMukaiyama-Michael reaction of α,β-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH 2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol%). This carbon acid-mediatedVMMreaction provides a powerful synthetic methodology to construct highly substituted γ-butenolide structure. 2010 American Chemical Society.
General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory Gorgonian lipid
Boukouvalas, John,Loach, Richard P.
, p. 8109 - 8112 (2008/12/22)
(Chemical Equation Presented) A variety of α-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.
Microwave assisted Suzuki reactions for the preparation of the antifungal 3-aryl-5-methyl-2,5-dihydrofuran-2-ones
Mathews, Christopher J.,Taylor, John,Tyte, Melloney J.,Worthington, Paul A.
, p. 538 - 540 (2007/10/03)
The Suzuki cross-coupling reaction of arylboronic acids with a bromo-furanone has been developed to prepare a series of substituted 2,5-dihydrofuran-2-ones related to the fungal metabolite, incrustoporin. A protocol of microwave heating was introduced to improve synthesis throughput. Georg Thieme Verlag Stuttgart.
Stepwise cross-couplings of a dibromo-γ-methylenebutenolide as an access to Z-configured α-alkenyl-γ-alkylidenebutenolides. Straightforward synthesis of the antibiotic lissoclinolide
Sorg, Achim,Blank, Frederik,Bruckner, Reinhard
, p. 1286 - 1290 (2007/10/03)
The Z-isomer of α-bromo-γ-(bromomethylene)butenolide was prepared from α-angelica lactone or levulinic acid in three and four steps, respectively. Successive Stille-couplings with an unsaturated stannane, with the potential to use a different second unsaturated stannane, involved the a?-substituent first and the a?-substituent thereafter. Thereby, α-alkenyl-γ-alkylidenebutenolides and their arene analogs were obtained Z-selectively.
TOTAL SYNTHESIS OF (+/-)-AVENACIOLIDE AND ITS ANALOGUES
Takei, Hisashi,Fukuda, Yoshimasa,Taguchi, Takeo,Kawara, Tatsuo,Mizutani, Hidemi,Mukuta, Takashi
, p. 1311 - 1314 (2007/10/02)
A new method for the stereoselective synthesis of (+/-)-avenaciolide and its analogues via methoxycarbonyl- or anisyloxycarbonyldi-γ-lactones, which could be easily prepared by the reaction of γ-substituted α-bromobutenolides with sodium salt of methyl or anisyl malonamate in good yields, was described.
