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Total syntheses and absolute stereochemistry of decarestrictines C1 and C2 |
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| Authors: | Debendra K Mohapatra Gokarneswar Sahoo Dhondi K Ramesh J Srinivasa Rao G Narahari Sastry |
| Institution: | aOrganic Chemistry Division, National Chemical Laboratory (CSIR), Pune 411 008, India;bOrganic Chemistry Division-I, Indian Insititute of Chemical Technology (CSIR), Hyderabad 500 007, India;cMolecular Modeling Group, Indian Insititute of Chemical Technology (CSIR), Hyderabad 500 007, India |
| 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. |
| Keywords: | Decarestrictines Sharpless asymmetric epoxidation Pinnick oxidation Yamaguchi coupling reaction Ring-closing metathesis |
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