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Asymmetric Synthesis of (+)-anti- And (-)-syn-Mefloquine Hydrochloride

Asymmetric Synthesis of (+)-anti- And (-)-syn-Mefloquine Hydrochloride

Ettore J Rastelli, Don M Coltart

J Org Chem. 2016 Oct 21;81(20):9567-9575.

PMID: 27657347

Abstract:

The asymmetric (er > 99:1) total synthesis of (+)-anti- and (-)-syn-mefloquine hydrochloride from a common intermediate is described. The Sharpless asymmetric dihydroxylation is the key asymmetric transformation used in the synthesis of this intermediate. It is carried out on an olefin that is accessed in three steps from commercially available materials, making the overall synthetic sequence very concise. The common diol intermediate derived from the Sharpless asymmetric dihydroxylation is converted into either a trans- or cis-epoxide, and these are subsequently converted to (+)-anti- and (-)-syn-mefloquine, respectively. X-ray crystallographic analysis of derivatives of (+)-anti- and (-)-syn-mefloquine is used to lay to rest a 40 year argument regarding the absolute stereochemistry of the mefloquines. A formal asymmetric (er > 99:1) synthesis of (+)-anti-mefloquine hydrochloride is also presented that uses a Sharpless asymmetric epoxidation as a key step.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP51773923-A	Mefloquine hydrochloride		51773-92-3	Price

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