Total synthesis of a hypothetical macroketone of migrastatin
| Title | Total synthesis of a hypothetical macroketone of migrastatin |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Choudhury, R, D. Reddy, S |
| Journal | European Journal of Organic Chemistry |
| Volume | 2021 |
| Issue | 21 |
| Pagination | 3050-3053 |
| Date Published | JUN |
| Type of Article | Article |
| ISSN | 1434-193X |
| Keywords | Hypothetical mecroketon, Metastasis, Migrastatin, RCM, vinylogous Mukaiyama aldol reaction (VMAR) |
| Abstract | Danishefsky's macroketone, a simplified analogue of natural product Migrastatin, is one of the lead compounds with potent cancer cell migration inhibition potential. Different biological assays suggest fascin protein as the potential target. Although it was indicated through X-ray co-crystallography where the concerned macroketone analogue was found to bind in the actin-binding sites of fascin, there was a structural discrepancy, as the X-ray co-crystal structure suggested an E-olefin along with inversion of methyl stereochemistry from that of Danishefsky's macroketone. Here, we have accomplished the total synthesis of the `hypothetical macroketone' for the first time. The TiCl4 mediated vinylogous Mukaiyama aldol reaction is the key step in present synthesis. |
| DOI | 10.1002/ejoc.202100484 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.021 |
Divison category:
Organic Chemistry
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