Kanikarapu, Suresh ; Marumudi, Kanakaraju ; Kunwar, Ajit C. ; Yadav, Jhillu S. ; Mohapatra, Debendra K. (2017) Total Synthesis and Stereochemical Revision of 4,8-Dihydroxy-3,4-dihydrovernoniyne Organic Letters, 19 (16). pp. 4167-4170. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/Acs.Orglett.7B01620
Related URL: http://dx.doi.org/10.1021/Acs.Orglett.7B01620
Abstract
The first asymmetric total synthesis of two possible diastereomers (4S,5R)-4,8-dihydroxy-3,4-dihydrovernoniyne 5 and (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne 5a is accomplished. Salient features of the synthesis involve Cadiot-Chodkiewicz coupling and Sonogashira cross-coupling of terminal acetylenes. Detailed comparison of the 1H and 13C NMR data and specific rotation with that of the natural product led to the revision of the absolute stereochemistry of the natural product as (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne 5a.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 135686 |
| Deposited On: | 10 Aug 2023 07:45 |
| Last Modified: | 10 Aug 2023 07:45 |
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