35630-42-3Relevant academic research and scientific papers
Metal-mediated reactions of α-bromomethyl-propenoate esters
Drewes,Taylor,Ramesar,Field
, p. 321 - 329 (1995)
Methyl 2-bromomethylprop-2-enoate reacts with benzaldehyde and with salicylaldehyde via its Sn and Zn complexes under aqueous conditions to form α-methylene-γ-lactones in high yields. In the case of salicylaldehyde X-ray analysis proves conclusively formation of a five- rather than a seven-membered ring. Under the above conditions 2-bromomethyl-3-phenylprop-2-enoate does not afford any cyclic products.
β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
Abutaleb, Nader S.,Hamann, Henry J.,Pal, Rusha,Ramachandran, P. Veeraraghavan,Seleem, Mohamed N.
supporting information, (2020/10/02)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthe
α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
Lloyd, Matthew G.,D'Acunto, Mariantonietta,Taylor, Richard J.K.,Unsworth, William P.
, p. 7107 - 7123 (2015/02/19)
Abstract A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
A one-pot C-H insertion/olefination sequence for the formation of α-alkylidene-γ-butyrolactones
Lloyd, Matthew G.,Taylor, Richard J. K.,Unsworth, William P.
, p. 2772 - 2775 (2014/06/09)
A one-pot C-H insertion/olefination sequence for the conversion of α-diazo-α-(dialkoxyphosphoryl)acetates into α-alkylidene- γ-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate cataly
Tailored α-methylene-γ-butyrolactones and their effects on growth suppression in pancreatic carcinoma cells
Ramachandran, P. Veeraraghavan,Pratihar, Debarshi,Nair, Hari Narayanan G.,Walters, Matthew,Smith, Sadie,Yip-Schneider, Michele T.,Wu, Huangbing,Schmidt, C. Max
supporting information; experimental part, p. 6620 - 6623 (2010/12/19)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) were synthesized via allylboration and screened against three human pancreatic cancer cell lines (Panc-1, MIA PaCa-2, and BxPC-3). This systematic study established a discernible relationsh
A facile indium-mediated synthesis of protected and unprotected [1- (hydroxymethyl)vinyl]alkanols
Moirangthem, Nimalini D.,Thingom, Bhavna,Laitonjam, Warjeet S.
scheme or table, p. 455 - 459 (2009/12/24)
Protected and unprotected [l-(hydroxymethyl)vinyl]alkanols (7 and 8) have been synthesized from the homologated y-hydroxy esters 4 which have been prepared by indium-mediated allylation of the rearranged bromides 3 derived from hydroxyl esters 2 in water medium.
α-Methylene-γ-butyrolactones with molluscicidal activity
Rucker,Hostettmann,Gajewski,Lobbert,Boken
, p. 941 - 945 (2007/10/02)
The α-methylene-γ-butyrolactones 1-28 were tested in vitro for molluscicidal activity against Biomphalaria glabrata. The racemic compound 25 shows the best activity. The synthesis was carried out by modified Reformatzky reaction of the corresponding carbo
PREPARATION AND SYNTHETIC APPLICATION OF 2-BROMOALLYLTRIMETHYLSILANE AS A 1-HYDROXYMETHYLVINYL ANION EQUIVALENT
Nishiyama, Hisao,Yokoyama, Hiroshi,Narimatsu, Shinzo,Itoh, Kenji
, p. 1267 - 1270 (2007/10/02)
The 1-trimethylsilylmethylvinyl group, as a 1-hydroxymethylvinyl equivalent, was readily introduced to epoxides with the corresponding Grignard reagent derived from 2-bromoallyltrimethylsilane.Obtained 2-(2-hydroxyethyl)-allylsilanes were converted to α-methylene-γ-lactones via diols.
