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35
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4644310762
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note
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The yield was increased to 76% in another experiment by using an 80:20 mixture of the enantiomers (1R,5S,6S)-(-)-(8) (94% ee) and (1R,5R,6R)-(+)-(9) (>98% ee), which lead to enantiomerically enriched (S,S)-methyl ester (+)-26. The enantiomers were obtained by enzyme-catalyzed hydrolysis [16] of fully acetylated rac-diols 2 and 3 (52%) followed by Jones oxidation of the free hydroxyl group.
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36
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4644303440
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Several years ago, the diastereomeric (R,S)-methyl ester was synthesized: V. N. Odinokov, L. P. Zhemaiduk, G. Yu. Ishmuratov, G. A. Tolstikov, Zh. Org. Khim. 1978, 14, 1617-1627; J. Org. Chem. Russ. Ed. 1978, 14, 1511-1518.
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Odinokov, V.N.1
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Ishmuratov, G.Yu.3
Tolstikov, G.A.4
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37
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4644255632
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Several years ago, the diastereomeric (R,S)-methyl ester was synthesized: V. N. Odinokov, L. P. Zhemaiduk, G. Yu. Ishmuratov, G. A. Tolstikov, Zh. Org. Khim. 1978, 14, 1617-1627; J. Org. Chem. Russ. Ed. 1978, 14, 1511-1518.
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39
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4644336787
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note
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G. M. Sheldrick, University of Göttingen, 1997.
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-
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40
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4644294116
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note
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E. Keller, University of Freiburg, 1997.
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