Yadav, J. S. ; Ganganna, B. ; Dutta, Palash ; Singarapu, Kiran K (2014) Synthesis and Determination of Absolute Configuration of α-Pyrones Isolated from Penicillium corylophilum Journal of Organic Chemistry, 79 (22). pp. 10762-10771. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo5015382
Related URL: http://dx.doi.org/10.1021/jo5015382
Abstract
The first total synthesis of (S)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of the proposed structural assignment of the natural product as (R)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one. The key steps include chiral auxiliary mediated asymmetric acetate aldol reaction, dianion addition, and base mediated cyclization to form an α-pyrone ring.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 135724 |
| Deposited On: | 10 Aug 2023 12:27 |
| Last Modified: | 10 Aug 2023 12:27 |
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