Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

James L. Carr; Jimmy J. P. Sejberg; Fabienne Saab; Mary D. Holdom; Anna M. Davies; Andrew J. P. White; Robin J. Leatherbarrow; Andrew J. Beavil; Brian J. Sutton; Stephen D. Lindell; Alan C. Spivey

doi:10.1039/c1ob05862b

Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

James L. Carr, Jimmy J. P. Sejberg, Fabienne Saab, Mary D. Holdom, Anna M. Davies, Andrew J. P. White, Robin J. Leatherbarrow, Andrew J. Beavil, Brian J. Sutton, Stephen D. Lindell, Alan C. Spivey^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FceRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein we report a novel approach to the synthesis of the C19 methyl ether of aspercyclide A, employing a Pd(0)-catalysed, fluorous-tagged alkenylgermane/arylbromide macrocyclisation (germyl-Stille reaction) as the key step, and evaluation of both enantiomers of this compound via ELISA following optical resolution by CSP-HPLC. A crystal structure for germyl hydride 27 is also reported.

Original language	English
Pages (from-to)	6814-6824
Journal	ORGANIC AND BIOMOLECULAR CHEMISTRY
Volume	9
Issue number	19
DOIs	https://doi.org/10.1039/c1ob05862b
Publication status	Published - 2011

Keywords

ROBUST
ALKYNES
REAGENTS
CHROMIUM
BIARYL SYNTHESIS
COPPER
COUPLING REACTIONS
ACETALS
DIARYL ETHERS
CATALYTIC C-C

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Carr, J. L., Sejberg, J. J. P., Saab, F., Holdom, M. D., Davies, A. M., White, A. J. P., Leatherbarrow, R. J., Beavil, A. J., Sutton, B. J., Lindell, S. D., & Spivey, A. C. (2011). Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution. ORGANIC AND BIOMOLECULAR CHEMISTRY, 9(19), 6814-6824. https://doi.org/10.1039/c1ob05862b

@article{c3c5ca4ae2c041c6b0f25fbb43bbad5b,

title = "Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution",

abstract = "Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FceRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein we report a novel approach to the synthesis of the C19 methyl ether of aspercyclide A, employing a Pd(0)-catalysed, fluorous-tagged alkenylgermane/arylbromide macrocyclisation (germyl-Stille reaction) as the key step, and evaluation of both enantiomers of this compound via ELISA following optical resolution by CSP-HPLC. A crystal structure for germyl hydride 27 is also reported.",

keywords = "ROBUST, ALKYNES, REAGENTS, CHROMIUM, BIARYL SYNTHESIS, COPPER, COUPLING REACTIONS, ACETALS, DIARYL ETHERS, CATALYTIC C-C",

author = "Carr, {James L.} and Sejberg, {Jimmy J. P.} and Fabienne Saab and Holdom, {Mary D.} and Davies, {Anna M.} and White, {Andrew J. P.} and Leatherbarrow, {Robin J.} and Beavil, {Andrew J.} and Sutton, {Brian J.} and Lindell, {Stephen D.} and Spivey, {Alan C.}",

year = "2011",

doi = "10.1039/c1ob05862b",

language = "English",

volume = "9",

pages = "6814--6824",

journal = "ORGANIC AND BIOMOLECULAR CHEMISTRY",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "19",

}

Carr, JL, Sejberg, JJP, Saab, F , Holdom, MD , Davies, AM, White, AJP, Leatherbarrow, RJ, Beavil, AJ , Sutton, BJ, Lindell, SD & Spivey, AC 2011, 'Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution', ORGANIC AND BIOMOLECULAR CHEMISTRY, vol. 9, no. 19, pp. 6814-6824. https://doi.org/10.1039/c1ob05862b

TY - JOUR

T1 - Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

AU - Carr, James L.

AU - Sejberg, Jimmy J. P.

AU - Saab, Fabienne

AU - Holdom, Mary D.

AU - Davies, Anna M.

AU - White, Andrew J. P.

AU - Leatherbarrow, Robin J.

AU - Beavil, Andrew J.

AU - Sutton, Brian J.

AU - Lindell, Stephen D.

AU - Spivey, Alan C.

PY - 2011

Y1 - 2011

N2 - Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FceRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein we report a novel approach to the synthesis of the C19 methyl ether of aspercyclide A, employing a Pd(0)-catalysed, fluorous-tagged alkenylgermane/arylbromide macrocyclisation (germyl-Stille reaction) as the key step, and evaluation of both enantiomers of this compound via ELISA following optical resolution by CSP-HPLC. A crystal structure for germyl hydride 27 is also reported.

AB - Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FceRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein we report a novel approach to the synthesis of the C19 methyl ether of aspercyclide A, employing a Pd(0)-catalysed, fluorous-tagged alkenylgermane/arylbromide macrocyclisation (germyl-Stille reaction) as the key step, and evaluation of both enantiomers of this compound via ELISA following optical resolution by CSP-HPLC. A crystal structure for germyl hydride 27 is also reported.

KW - ROBUST

KW - ALKYNES

KW - REAGENTS

KW - CHROMIUM

KW - BIARYL SYNTHESIS

KW - COPPER

KW - COUPLING REACTIONS

KW - ACETALS

KW - DIARYL ETHERS

KW - CATALYTIC C-C

U2 - 10.1039/c1ob05862b

DO - 10.1039/c1ob05862b

M3 - Article

SN - 1477-0520

VL - 9

SP - 6814

EP - 6824

JO - ORGANIC AND BIOMOLECULAR CHEMISTRY

JF - ORGANIC AND BIOMOLECULAR CHEMISTRY

IS - 19

ER -

Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution

Abstract

Keywords

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