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Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.

Original publication

DOI

10.1021/ol3020607

Type

Journal article

Journal

Org Lett

Publication Date

17/08/2012

Volume

14

Pages

4278 - 4281

Keywords

Carboxylic Acids, Cocaine, Molecular Structure, Stereoisomerism, Tropanes