Maity, Saurabh ; Kanikarapu, Suresh ; Marumudi, Kanakaraju ; Kunwar, Ajit C. ; Yadav, Jhillu S. ; Mohapatra, Debendra K. (2017) Asymmetric Total Synthesis of the Putative Structure of Diplopyrone Journal of Organic Chemistry, 82 (9). pp. 4561-4568. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/Acs.Joc.7B00086
Related URL: http://dx.doi.org/10.1021/Acs.Joc.7B00086
Abstract
The first asymmetric total synthesis of the putative structure of diplopyrone was achieved in 17 linear steps starting from cis-1,4-butene-diol. The synthetic route features iodine-catalyzed tandem isomerization followed by C-O and C-C bond formation reaction strategy developed by our own group to construct the trans-2,6-disubstituted dihydropyran ring, asymmetric α-aminoxylation reaction, and Still-Gennari (Z)-selective olefination reactions. Careful comparison of 1H and 13C NMR spectroscopic data as well as investigation of the UV and circular dichroism spectrum in trifluoroethanol for compound 2 suggest that the putative structure for diplopyrone {6-[(1S)-1-hydroxyethyl]-2,4a(S),6(R),8a(S)-tetrahydropyran[3,2-b]pyran-2-one} requires revision.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 135687 |
| Deposited On: | 10 Aug 2023 07:46 |
| Last Modified: | 10 Aug 2023 07:46 |
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