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

Research output: Contribution to journal › Article › peer-review

25 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

Access to Document

10.1021/jo9822232

Cite this

@article{04b704da49514e53b1b8e927eaa4cbe3,

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",

month = apr,

day = "2",

doi = "10.1021/jo9822232",

language = "English (US)",

volume = "64",

pages = "2411--2417",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "7",

}

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.

UR - http://www.scopus.com/inward/record.url?scp=0033515462&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033515462&partnerID=8YFLogxK

U2 - 10.1021/jo9822232

DO - 10.1021/jo9822232

M3 - Article

AN - SCOPUS:0033515462

SN - 0022-3263

VL - 64

SP - 2411

EP - 2417

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Semisynthesis of an antifungal lipopeptide echinocandin

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this