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gem -Dihalogenocyclopropanes as building blocks in natural product synthesis: enantioselective total syntheses of ent -erythramine and 3- epi -erythramine

Stanislawski, Pauline; Willis, Anthony; Banwell, Martin

Description

ent-Erythramine ((-)-1), the enantiomer of the alkaloid erythramine, was prepared in 15 steps from known compounds. The first of three pivotal bond-forming steps in the synthesis was a Suzuki-Miyaura cross-coupling reaction of the starting materials to give a bis-silyl ether. The second involved silver(I)-induced electrocyclic ring opening of the gem-dichlorocyclo-propane formed in the next step and trapping of the ensuing π-allyl cation by the tethered nitrogen atom to give, following cleavage...[Show more]

CollectionsANU Research Publications
Date published: 2007
Type: Journal article
URI: http://hdl.handle.net/1885/33413
Source: Chemistry - An Asian Journal
DOI: 10.1002/asia.200700155

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