Regioselective Oxidation of (+)-α-Longipinene by Aspergillus niger

Kazuki Sakata; Mitsuo Miyazawa

doi:10.5650/jos.59.261

Chemistry and Organic Synthesis

Regioselective Oxidation of (+)-α-Longipinene by Aspergillus niger

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Keywords: (+)-α-longipinene, (+)-(5S)-5,12-dihydroxy-α-longipinene, (-)-(5R)-5,12-dihydroxy-α-longipinene, (+)-12-hydroxy-α-longipinen-5-one, Aspergillus niger

JOURNAL FREE ACCESS

2010 Volume 59 Issue 5 Pages 261-265

DOI https://doi.org/10.5650/jos.59.261

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Abstract

The regioselective oxidation of (+)-α-longipinene (1) with sesquiterpen hydrocarbon was investigated using Aspergillus niger (NBRC 4414) as a biocatalyst. Compound 1 was converted to three new terpenoids, (+)-(5S)-5,12-dihydroxy-α-longipinene (2), (-)-(5R)-5,12-dihydroxy-α-longipinene (3), and (+)-12-hydroxy-α-longipinen-5-one (4). These structures were determined by NMR, IR, specific rotation and mass spectral studies.

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