NMR studies on chiral intermediates in the total synthesis of (+)-biotin from D-mannose
β Scribed by Wen-xue Chen; Ping Zhang; Fen-er Chen
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 138 KB
- Volume
- 48
- Category
- Article
- ISSN
- 0749-1581
- DOI
- 10.1002/mrc.2619
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β¦ Synopsis
Abstract
The chemical structure and stereochemistry of 12 intermediates in the total synthesis of (+)βbiotin starting from Dβmannose as chiral pool were completely assigned using oneβ and twoβdimensional NMR experiments, including 1D selective NOE, DEPT, COSY, HSQC and HMBC. Copyright Β© 2010 John Wiley & Sons, Ltd.
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Preparation of the "Ziegler key intermediate" 2from lactone 3, readily obtained from hydroxy-O-ionone, was studied. In a first exploratory approach, lactones 11 and 13 were obtained but further transformations aimed at setting the ring junction were unsuccessful due to unexpected rearrangements. Thr
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