161254-27-9Relevant academic research and scientific papers
Transition Metal-Catalyzed, Chlorine-Transfer Radical Cyclizations of 2-(3-Alken-1-oxy)-2-chloroacetates. Formal Total Synthesis of Avenaciolide and Isoavenaciolide
Udding, Jan H.,Tuijp, Kees (C.) J. M.,Zanden, Marco N. A. van,Hiemstra, Henk,Speckamp, W. Nico
, p. 1993 - 2003 (2007/10/02)
A novel method for the synthesis of functionalized tetrahydrofurans is described.This method involves the treatment of 2-(3-alken-1-oxy)-2-chloroacetates 1 with a catalytic amount of Cu(bpy)Cl in refluxing 1,2-dichloroethane to give good yields of 3-(1-ch
Xanthate Transfer Cyclization of Glycolic Acid-Derived Radicals. Synthesis of Five- to Eight-Membered Ring Ethers
Udding, Jan H.,Giesselink, J. P. M.,Hiemstra, Henk,Speckamp, W. Nico
, p. 6671 - 6682 (2007/10/02)
A novel method for the preparation of functionalized five- to eight-membered ring ethers is described.This method involves the xanthate transfer radical cyclization of 2-(alken-1-oxy)-2-acetic acid methyl esters 6 to give good yields of xanthate-substituted five- to eight-membered ethers 7 and/or 8, depending on the length of the carbon chain.These cyclic ethers are usually obtained as mixtures of diastereomers.The cyclizations are performed at 150-160 deg C in tert-butylbenzene with di-tert-butyl peroxide as the initiator.This group-transfer radical cyclization was successfully applied in a total synthesis of lauthisan (44).The use of benzoyl xanthate (56) as a catalyst allows a visible light-induced xanthate transfer cyclization to a tetrahydrofuran in high yield.
