Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B
Author:
Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference23 articles.
1. For example, see: (a) Grabley, S.; Granzer, E.; Huetter, K.; Ludwig, D.; Mayer, M.; Thiericke, R.; Till, G.; Phillipps, S.; Wink, J.; Zeeck, A. J. Antibiot. 1992, 45, 56–65;
2. (b) Nagle, D. G.; Gerwick, W. H. J. Org. Chem. 1994, 59, 7227–7237;
3. (c) Arnone, A.; Nasini, G.; de Pava, O. V. Phytochemistry, 2000, 53, 1087–1090.
4. Ethylenic diols 2 or their Z isomers are easily obtainable from 1 by LiAlH4 reduction and partial hydrogenation, respectively. These substrates are potentially amenable to transformation into other functionalities in a stereoselective way (see, for instance, Refs. 3–5). For a review on substrate-directable chemical reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307–1370.
5. Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols
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