gem -Dihalogenocyclopropanes as building blocks in natural product synthesis: enantioselective total syntheses of ent -erythramine and 3- epi -erythramine
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]
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|Source:||Chemistry - An Asian Journal|
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