Mohapatra, Debendra K. ; Sahoo, Gokarneswar ; Ramesh, Dhondi K. ; Rao, J. Srinivasa ; Sastry, G. Narahari (2009) Total syntheses and absolute stereochemistry of decarestrictines C1 and C2 Tetrahedron Letters, 50 (40). pp. 5636-5639. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.07.099
Abstract
The total syntheses of decarestrictines C1 and C2 have been described. The synthetic strategy involves a practical and flexible approach using esterification and ring-closing metathesis to unite the acid and alcohol fragments. The acid fragments are enantiomers of each other and have been prepared from l-(−)-malic acid via similar transformations; in Sharpless asymmetric epoxidation, (+)-DET has been used for decarestrictine C1 and (−)-DET for decarestrictine C2. The alcohol fragment is identical for both decarestrictines C1 and C2 and has been accessed from d-(+)-mannitol. Comparison of the 1H and 13C NMR data combined with the computational studies predicts the presence of two conformations without and with hydrogen bonding (conformational isomers I and II for decarestrictine C1), respectively. The 1H and 13C NMR data for decarestrictine C2 completely agreed with the analytical data reported by Kibayashi et al.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Decarestrictines; Sharpless Asymmetric Epoxidation; Pinnick Oxidation; Yamaguchi Coupling Reaction; Ring-Closing Metathesis |
| ID Code: | 108032 |
| Deposited On: | 28 Jul 2017 05:58 |
| Last Modified: | 28 Jul 2017 05:58 |
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