Organic Letters
Organic Letters
5 years ago

Total Synthesis and Stereochemical Revision of 4,8-Dihydroxy-3,4-dihydrovernoniyne

Total Synthesis and Stereochemical Revision of 4,8-Dihydroxy-3,4-dihydrovernoniyne
Jhillu S. Yadav, Ajit C. Kunwar, Kanakaraju Marumudi, Suresh Kanikarapu, Debendra K. Mohapatra
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01620

DOI: 10.1021/acs.orglett.7b01620

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