Abstract
Compound 1 is a macrocyclic lipopeptide belonging to the echinocandin family, which has been effective in treating systemic fungal infections. In this paper, we report a unique regio-, chemo-, and stereoselective synthesis of 1 in four steps from the deacylated nucleus 3 in an impressive 83% overall yield. Highlights of this synthesis include a selective reduction of the amide to the amine and a highly stereoselective (99:1 α/β) introduction of the 2-aminoethyl hemiaminal. In addition, the synthesis of the naphthoyl side chain was accomplished in three steps in 79% overall isolated yield from commercially available 6-bromo-2-naphthol.
Original language | English (US) |
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Pages (from-to) | 2411-2417 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 64 |
Issue number | 7 |
DOIs | |
State | Published - Apr 2 1999 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Organic Chemistry