Semisynthesis of an antifungal lipopeptide echinocandin

被引：17

作者：

Journet, M ^{[1
]}

Cai, DW ^{[1
]}

DiMichele, LM ^{[1
]}

Hughes, DL ^{[1
]}

Larsen, RD ^{[1
]}

Verhoeven, TR ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Sharp & Dohme Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 07期

关键词：

D O I：

10.1021/jo9822232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha/beta) 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.

引用

页码：2411 / 2417

页数：7

共 18 条

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