Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil

Horacio F. Olivo; Antonio Osorio-Lozada; Tonya L. Peeples

doi:10.1016/j.tetasy.2005.07.028

Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil

Horacio F. Olivo
, Antonio Osorio-Lozada
, Tonya L. Peeples

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.

Original language	English (US)
Pages (from-to)	3507-3511
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	21
DOIs	https://doi.org/10.1016/j.tetasy.2005.07.028
State	Published - Oct 31 2005

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2005.07.028

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title = "Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil",

abstract = "A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.",

author = "Olivo, \{Horacio F.\} and Antonio Osorio-Lozada and Peeples, \{Tonya L.\}",

note = "Funding Information: This research was supported by the National Science Foundation (EEC-0310689). We thank Prof. Jack Rosazza for his invaluable advice and encouragement. We thank Proffers. Rebecca Parales (U California-Davis) and David T. Gibson (U Iowa) for the E. coli NDO and TDO, Prof. Marko Mihovilovic (U Austria) for the E. coli CHMO and CPMO, Prof. Karl-H. Engesser (U Stuttgart) for Sphingomonas sp. HXN-200, and Dr. Kerry O{\textquoteright}Donnell (USDA) for Helminthosporium strains. ",

year = "2005",

month = oct,

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doi = "10.1016/j.tetasy.2005.07.028",

language = "English (US)",

volume = "16",

pages = "3507--3511",

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T1 - Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil

AU - Olivo, Horacio F.

AU - Osorio-Lozada, Antonio

AU - Peeples, Tonya L.

N1 - Funding Information: This research was supported by the National Science Foundation (EEC-0310689). We thank Prof. Jack Rosazza for his invaluable advice and encouragement. We thank Proffers. Rebecca Parales (U California-Davis) and David T. Gibson (U Iowa) for the E. coli NDO and TDO, Prof. Marko Mihovilovic (U Austria) for the E. coli CHMO and CPMO, Prof. Karl-H. Engesser (U Stuttgart) for Sphingomonas sp. HXN-200, and Dr. Kerry O’Donnell (USDA) for Helminthosporium strains.

PY - 2005/10/31

Y1 - 2005/10/31

N2 - A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.

AB - A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.

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UR - https://www.scopus.com/pages/publications/27944454780#tab=citedBy

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DO - 10.1016/j.tetasy.2005.07.028

M3 - Article

AN - SCOPUS:27944454780

SN - 0957-4166

VL - 16

SP - 3507

EP - 3511

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 21

ER -

Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil

Abstract

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