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Title: A carbohydrate-based synthesis of fused bicyclic ethers by radical cyclization of epoxides using titanocene(III) chloride
Authors: Jana, S
Guin, C
Roy, S C
Keywords: Bicyclic ethers;Carbohydrate;Radical cyclization;Epoxides;Transition-metal
Issue Date: Oct-2007
Publisher: CSIR
Abstract: A carbohydrate-based synthesis of both cis- and trans-fused bicylic ethers has been achieved by radical cyclization of epoxides using a transition-metal radical source. Thus, 6-exo radical cyclizations of the carbohydrate derivatives using [bis(cyclopentadienyl)titanium(III)]chloride (Cp₂TiCl) as the radical source has resulted in corresponding cis- and trans-fused bicyclic ethers. While the trans-fused compound has allowed stereoselective radical cyclization, the cis-fused has ended up only in a mixture of isomers. The functionalities present in the bicyclic compounds are potential intermediates as multifunctional conformationally rigid scaffolds.
Page(s): 1648-1657
ISSN: 0376-4699
Appears in Collections:IJC-B Vol.46B(10) [October 2007]

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