Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5278719 | Tetrahedron Letters | 2009 | 4 Pages |
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-(â)-malic acid via similar transformations; in Sharpless asymmetric epoxidation, (+)-DET has been used for decarestrictine C1 and (â)-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.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Debendra K. Mohapatra, Gokarneswar Sahoo, Dhondi K. Ramesh, J. Srinivasa Rao, G. Narahari Sastry,