Journal of Organic Chemistry p. 6671 - 6682 (1994)
Update date:2022-08-04
Topics:
Udding, Jan H.
Giesselink, J. P. M.
Hiemstra, Henk
Speckamp, W. Nico
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-<(ethoxythiocarbonyl)sulfanyl>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.
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