Semisynthesis of an antifungal lipopeptide echinocandin

M. Journet; D. Cai; L. M. Dimichele; D. L. Hughes; R. D. Larsen; T. R. Verhoeven; P. J. Reider

doi:10.1021/jo9822232

Semisynthesis of an antifungal lipopeptide echinocandin

M. Journet, D. Cai, L. M. Dimichele, D. L. Hughes, R. D. Larsen, T. R. Verhoeven, P. J. Reider

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10 Scopus citations

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)
Pages (from-to)	2411-2417
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	64
Issue number	7
DOIs	https://doi.org/10.1021/jo9822232
State	Published - Apr 2 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Semisynthesis of an antifungal lipopeptide echinocandin",

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.",

author = "M. Journet and D. Cai and Dimichele, {L. M.} and Hughes, {D. L.} and Larsen, {R. D.} and Verhoeven, {T. R.} and Reider, {P. J.}",

year = "1999",

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doi = "10.1021/jo9822232",

language = "English (US)",

volume = "64",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Semisynthesis of an antifungal lipopeptide echinocandin

AU - Journet, M.

AU - Cai, D.

AU - Dimichele, L. M.

AU - Hughes, D. L.

AU - Larsen, R. D.

AU - Verhoeven, T. R.

AU - Reider, P. J.

PY - 1999/4/2

Y1 - 1999/4/2

N2 - 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.

AB - 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.

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DO - 10.1021/jo9822232

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JF - Journal of Organic Chemistry

IS - 7

ER -

Semisynthesis of an antifungal lipopeptide echinocandin

Abstract

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