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Stereoselective reduction of (±)-bicyclo[3.3.1]nonane-2,6-dione by microorganisms

✍ Scribed by Mitsuo Miyazawa; Masahiro Nobata; Shigeaki Okamura; Osamu Muraoka; Genzoh Tanabe; Hiromu Kameoka

Publisher
Wiley (John Wiley & Sons)
Year
1998
Tongue
English
Weight
277 KB
Volume
71
Category
Article
ISSN
0268-2575

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✦ Synopsis

The biotransformation of (^)-bicyclo [3.3.1]nonane-2,6-dione by Aspergillus niger and Glomerella cingulata was investigated. The diketone was reduced to the ketoalcohol 2-endo-hydroxy-bicyclo[3.3.1]nonane-6-one and the diol endo,endo-bicyclo[3.3.1]nonane-2,6-diol respectively. Endo,endobicyclo[3.3.1]nonane-2,6-diol and ketoalcohols produced by G. cingulata had high optical purity, on the other hand, reduction by A. niger yielded optically active ([)-(1R, 2S, 5R, 6S)-bicyclo[3.3.1]nonane-2,6-diol(99É9% e.e.). 1998 SCI (

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Determination of the absolute configuration of bicyclo[3.3.1]nonane-2,7-dione by circular dichroism spectroscopy and chemical correlation
✍ Eugenius Butkus; Sigitas Stončius; Albinas Žilinskas 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 126 KB

## Abstract A study of the enantiomers of bicyclo[3.3.1]nonane‐2,7‐dione, a chiral molecule containing two carbonyl chromophores, was performed. Enantiomers of this structure were obtained by HPLC resolution and the (+)‐(1R,5S)‐enantiomer by enantiospecific synthesis from(+)‐(1S,5S)‐bicyclo[3.3.1]n