Towards stable di-carba analogues of guanofosfocins

Jan Duchek; Mu Hua Huang; Andrea Vasella

doi:10.1016/j.tetlet.2011.02.102

Towards stable di-carba analogues of guanofosfocins

Jan Duchek, Mu Hua Huang, Andrea Vasella^*

^*Corresponding author for this work

Swiss Federal Institute of Technology Zurich

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

3 Citations (Scopus)

Abstract

Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield.

Original language	English
Pages (from-to)	2940-2942
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2011.02.102
Publication status	Published - 8 Jun 2011
Externally published	Yes

Keywords

Antifungals
Carbohydrates
Heterocycles
Synthesis

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10.1016/j.tetlet.2011.02.102

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abstract = "Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield.",

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author = "Jan Duchek and Huang, {Mu Hua} and Andrea Vasella",

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T1 - Towards stable di-carba analogues of guanofosfocins

AU - Duchek, Jan

AU - Huang, Mu Hua

AU - Vasella, Andrea

PY - 2011/6/8

Y1 - 2011/6/8

N2 - Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield.

AB - Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield.

KW - Antifungals

KW - Carbohydrates

KW - Heterocycles

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=79955695916&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.02.102

DO - 10.1016/j.tetlet.2011.02.102

M3 - Article

AN - SCOPUS:79955695916

SN - 0040-4039

VL - 52

SP - 2940

EP - 2942

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Towards stable di-carba analogues of guanofosfocins

Abstract

Keywords

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