Preparation of all stereoisomers of 2-allyl-2-methyl-3-hydroxycyclopentanone by desymmetric processes based on a microbial oxidation and reduction system

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• 作者：Mikio Fujii ; Minoru Takeuchi ; Hiroyuki Akita ; Kaoru Nakamura
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：26 August 2009
• 年：2009
• 卷：50
• 期：34
• 页码：4941-4944
• 全文大小：398 K

文摘

All stereoisomers of 2-allyl-3-hydroxy-2-methylcyclopentanones 2–5 were prepared in high conversion and in an optically pure form by microbial reduction and oxidation. The reduction of symmetric diketone 1 by Geotrichum candidum NBRC 4597 under anaerobic conditions gave 2 in 83 % yield (98 % conversion), >99 % de, and >99 % ee, whereas the reduction of 1 by G. candidum NBRC 5767 under aerobic conditions gave 3 in 75 % yield (99 % conversion), >99 % de, and >99 % ee. Oxidation of meso-diol 6 by G. candidum NBRC 5767 under aerobic conditions afforded 4 in 83 % yield (99 % conversion) and >99 % ee, while oxidation of meso-diol 7 by Mucor heimalis IAM 6095 in the presence of cyclohexanone as a co-oxidant afforded 5 in 68 % yield (75 % conversion) and >99 % ee.