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Formal total synthesis of enigmazole A |
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| Authors: | Andreas Meissner Takayuki Kishi Yuka Fujisawa Yuto Murai Hiroyoshi Takamura Isao Kadota |
| Institution: | Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kitaku, Okayama 700-8530, Japan |
| Abstract: | A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A. |
| Keywords: | Enigmazole A Total synthesis Convergent synthesis Macrolide Allylation Reductive acetylation |
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