27610-27-1Relevant articles and documents
Synthesis of the C14-C28 fragment of tetronasin
Bourque, Elyse,Kocienski, Philip J.,Stocks, Michael,Yuen, Josephine
, p. 3219 - 3224 (2007/10/03)
A synthesis of the C14-C28 fragment of Tetronasin features an S E2 reaction between a cationic η3-allylmolybdenum complex and and an α-metallated tetrahydrofuran. Georg Thieme Verlag Stuttgart.
Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenes with a water-soluble radical initiator in aqueous media: Facile synthesis of γ-lactones
Yorimitsu,Wakabayashi,Shinokubo,Oshima
, p. 1963 - 1970 (2007/10/03)
Radical reactions in water or aqueous ethanol using a water-soluble radical initiator are described. Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis 4-cyanopentanoic acid), afforded 5-(4-hydroxybutyl)dihydrofuran-2(3H)-one in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93% yield. The reaction of 2-iodoacetamide with 1-octene in aqueous ethanol was initiated by 2,2′-azobis(2-methylpropanamidine) dihydrochloride to provide γ-decanolactone. Employing water as a solvent is crucial to obtain lactone in satisfactory yield.
(+/-)-erythro-γ,δ-Dihydroxycarboxylic Acid Lactones from a β-Lithiopropionate Equivalent and α-Chloroaldehydes
Plewe, Michael,Schmidt, Richard R.
, p. 534 - 536 (2007/10/02)
Reaction of β-ethylthio-β-lithioacrylate 1A with α-chloroaldehydes furnished predominantly the erythro products 3, which were isolated as γ-lactones 4.At room temperature intermediates 3 are transformed into the (+/-)-erythro-γ,δ-dihydroxycarboxylic acid γ-lactones 8.Raney nickel treatment provided interesting natural γ-lactone derivatives; thus, from erythro-8c the socalled L-factor erythro-9c was obtained.Similarly, from β-methoxy β-lithioacrylate 10A the (+/-)-erythro-γ,δ-dihydroxycarboxylic acid δ-lactone erythro-11 was gained.
A Simple, General Diastereoselective Synthesis of 5-Hydroxyalkylbutan-4-olides
Jefford, Charles W.,Wang, Ying
, p. 1513 - 1514 (2007/10/02)
cis- and trans-Hex-4-enoic acids and their 6-n-propyl and n-butyl derivatives, when treated with a 1.1 molar excess of m-chloroperbenzoic acid and Amberlyst-15 as catalyst in CH2Cl2 at 20 deg C, gave the corresponding threo- and erythro-5-hydroxyalkylbutan-4-olides in quantitative yields.