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Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine From Phenethyl Acetate

Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine From Phenethyl Acetate

Mary A A Endoma-Arias, Tomas Hudlicky

Chemistry. 2016 Oct 4;22(41):14540-3.

PMID: 27505136

Abstract:

The stereoselective total synthesis of unnatural (+)-galanthamine starting from phenethyl acetate is described. Chirality was introduced via microbial dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) to the corresponding cis-cyclohexadi-enediol, configuration of which provided the absolute stereochemistry of the ring C of (+)-galanthamine. Intramolecular Heck cyclization was used to form the quaternary carbon and dibenzofuran functionality. The synthesis of (+)-galanthamine was completed in a total of ten steps and an overall yield of 5.5 %. Experimental and spectral data are provided for all new compounds.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP103457	Phenethyl acetate		103-45-7	Price

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