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.
Original language | English |
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Pages (from-to) | 4492-4495 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 59 |
Issue number | 51 |
DOIs | |
Publication status | Published - Dec 19 2018 |
Keywords
- Allylation
- Convergent synthesis
- Enigmazole A
- Macrolide
- Reductive acetylation
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry