Total synthesis of (+/-)-powelline and (+/-)-buphanidrine.

Bogle KM, Hirst DJ, Dixon DJ

The total synthesis of (+/-)-powelline (13 linear steps in an overall yield of 6%) and (+/-)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.

Keywords:

Amaryllidaceae Alkaloids

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Crystallography, X-Ray

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Liliaceae

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Models, Molecular

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Molecular Structure

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Phenanthridines

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Stereoisomerism