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Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone From Phenethyl Acetate

Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone From Phenethyl Acetate

Mary Ann Endoma-Arias, Helen Dela Paz, Tomas Hudlicky

Molecules. 2019 Sep 25;24(19):3477.

PMID: 31557873

Abstract:

The total synthesis of (+)-10-keto-oxycodone was attained from phenethyl acetate in a stereoselective manner. Absolute stereochemistry was established via enzymatic dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) that furnished the corresponding cis-cyclohexadienediol whose configuration corresponds to the absolute stereochemistry of the ring C of (+)-10-keto-oxycodone. Intramolecular Heck reaction was utilized to establish the quaternary carbon at C-13, along with the dibenzodihydrofuran functionality. The C-14 hydroxyl and C-10 ketone were installed via SmI2-mediated radical cyclization, and oxidation of a benzylic alcohol (obtained from an intermediate nitrate azide), respectively. The synthesis of (+)-10-keto-oxycodone was completed in a total of 14 operations (21 steps) and an overall yield of ~2%. Experimental and spectral data are provided for key intermediates and 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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