- Preparative Bioorganic Chemistry, XVII. Reduction of a Prochiral Diketone, 9-Methyl-trans-decalin-1,8-dione, with Baker's Yeast
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Reduction of 9-methyl-trans-decalin-1,8-dione (1) with baker's yeast affords (8S,9R,10R)-8-hydroxy-9-methyl-trans-1-decalone (8) as the major product in 47percent yield.Its (8S,9S,10S)-isomer (9, 14percent yield) and (1S,8S)-9-methyl-trans-1,8-diol (10, 7percent yield) are obtained as minor products.Baker's yeast cannot reduce 9-methyl-cis-decalin-1,8-dione (2). Key Words: Asymmetric reduction / Baker's yeast / Yeast / Saccharomyces cerevisia / Enzymes / trans-1-Decalone derivatives / trans-1,8-Decalindione derivatives
- Mori, Kenji,Takayama, Shuichi,Yoshimura, Seiji
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- A new enantioselective approach to the bicyclo[4.4.0]decane and bicyclo[4.3.0]nonane systems
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Highly diasteroselective routes to cis-fused bicyclo[4.4.0]decane-2,10-diones and bicyclo[4.3.0]nonane-2,9-diones from 5-trimethylsilyl-2-cyclohexen-1 -one (1a) and its 3-methyl derivative were established by utilizing an annulation with Ω-(alkoxycarbonyl
- Asaoka,Nishimura,Takei
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p. 407 - 411
(2007/10/02)
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- PREPARATION OF BYCYCLOOCTANE-2,8-DIONE- AND DECALIN-1,8-DIONE-DERIVATIVES
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Alkylation of bicyclooctane-2,8-dione (1), which is prepared by a modification of the procedure described in the literature, gives the methyl- and propynyl-derivatives 6 and 7 (Scheme 1).In addition to the method described previously (Scheme 2), 9-
- Duthaler, Rudolf O.,Maienfisch, Peter
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p. 856 - 865
(2007/10/02)
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