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The First Stereoselective Total Synthesis of Naturally Occurring,Bioactive (3R,5R)‐1‐(4‐Hydroxyphenyl)‐7‐phenylheptane‐3,5‐diol and the Synthesis of Its Enantiomer |
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| Authors: | Parigi Raghavendar Reddy Chithaluri Sudhakar Jayprakash Narayan Kumar Biswanath Das |
| Institution: | 1. Organic Chemistry Division‐I, CSIR‐Indian Institute of Chemical Technology, Hyderabad‐500 007, India (phone: +91‐40‐7193434;2. fax: +91‐40‐7160512) |
| Abstract: | The first stereoselective total synthesis of the naturally occurring anti‐emetic diarylheptanoid (3R,5R)‐1‐(4‐hydroxyphenyl)‐7‐phenylheptane‐3,5‐diol ( 1 ) was accomplished starting from 4‐hydroxybenzaldehyde and involving a Sharpless kinetic resolution and an asymmetric epoxidation as the key steps (Scheme 2). The enantiomer 1a of this compound was also simultaneously prepared. |
| Keywords: | Alpinia officinarum Heptane‐3 5‐diol (3R 5R)‐1‐(4‐hydroxyphenyl)‐7‐phenyl‐ Stereoselective synthesis Sharpless epoxidation |