Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction.

Robert B. Grossman; Steven V. Ley

doi:10.1016/S0040-4020(01)89292-9

Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction.

Robert B. Grossman, Steven V. Ley

Chemistry

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

14 Scopus citations

Abstract

The synthesis of model compounds of azadirachtin containing the tetrahydrofurancarboxylate hemiketal functional group was achieved. The course of the oxidative ring contraction reaction that was used to form this functional group was observed to be unusually sensitive to the nature of substituents remote from the reactive centre.

Original language	English
Pages (from-to)	11553-11568
Number of pages	16
Journal	Tetrahedron
Volume	50
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4020(01)89292-9
State	Published - 1994

Bibliographical note

Funding Information:
Acknowledgements: We thank C. Hester Wallis and Maria-Lux de la Puente for synthetic assistance, and Drs. Andrew J. Edwards and Paul R. Raithby for the determination of the crystal stmctures. We would lie to thank the National Science Foundation for a NSF-NATO Post-Doctoral Fellowship (to RBG) and Ciba for further post-doctoral support. We also acknowledge financial support from Pfizer Central Research and the BP Research Endowment (to SVL).

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction.",

abstract = "The synthesis of model compounds of azadirachtin containing the tetrahydrofurancarboxylate hemiketal functional group was achieved. The course of the oxidative ring contraction reaction that was used to form this functional group was observed to be unusually sensitive to the nature of substituents remote from the reactive centre.",

author = "{B. Grossman}, Robert and {V. Ley}, Steven",

note = "Funding Information: Acknowledgements: We thank C. Hester Wallis and Maria-Lux de la Puente for synthetic assistance, and Drs. Andrew J. Edwards and Paul R. Raithby for the determination of the crystal stmctures. We would lie to thank the National Science Foundation for a NSF-NATO Post-Doctoral Fellowship (to RBG) and Ciba for further post-doctoral support. We also acknowledge financial support from Pfizer Central Research and the BP Research Endowment (to SVL).",

year = "1994",

doi = "10.1016/S0040-4020(01)89292-9",

language = "English",

volume = "50",

pages = "11553--11568",

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Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction. / B. Grossman, Robert; V. Ley, Steven.
In: Tetrahedron, Vol. 50, No. 39, 1994, p. 11553-11568.

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

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T1 - Chemistry of insect antifeedants from Azadirachta indica (Part 17)

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AU - B. Grossman, Robert

AU - V. Ley, Steven

N1 - Funding Information: Acknowledgements: We thank C. Hester Wallis and Maria-Lux de la Puente for synthetic assistance, and Drs. Andrew J. Edwards and Paul R. Raithby for the determination of the crystal stmctures. We would lie to thank the National Science Foundation for a NSF-NATO Post-Doctoral Fellowship (to RBG) and Ciba for further post-doctoral support. We also acknowledge financial support from Pfizer Central Research and the BP Research Endowment (to SVL).

PY - 1994

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AB - The synthesis of model compounds of azadirachtin containing the tetrahydrofurancarboxylate hemiketal functional group was achieved. The course of the oxidative ring contraction reaction that was used to form this functional group was observed to be unusually sensitive to the nature of substituents remote from the reactive centre.

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Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction.

Abstract

Bibliographical note

ASJC Scopus subject areas

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