Bakers yeast-catalyzed synthesis of optically pure 4-tert-butyl-3-hydroxy beta-lactam cis-(3R,4S) and trans-(3R,4R) diastereomers
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Baker's yeast (Saccharomyces cerevisiae) reductions were applied to the synthesis of the paclitaxel C-13 side-chain analogue. An easily synthesized alpha-keto-beta-lactam (1-(4-methoxyphenyl)-4-tert-butylazetidin-2,3-dione, 4) was reduced by yeast cells to give a mixture of enantiomerically pure cis and trans isomers. Both compounds were isolated and characterized, and their absolute configurations were confirmed by X-ray crystallographic analysis.Key words: Taxol®, C-13 side-chain, paclitaxel analogues, optically pure alpha-hydroxy-beta-lactams, baker's yeast-catalyzed reductions.
1991 ◽
Vol 1991
(4)
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pp. 397-398
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2009 ◽
Vol 75
(9)
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pp. 2765-2774
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1981 ◽
Vol 31
(1)
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pp. 290-294
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1974 ◽
Vol 8
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pp. 195-200
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2001 ◽
Vol 12
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pp. 1871-1879
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1981 ◽
Vol 45
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pp. 2713-2721