Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal v

Kiel E. Lazarski; Berkcan Akpinar; Regan J. Thomson

doi:10.1016/j.tetlet.2012.11.135

Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal v

Kiel E. Lazarski, Berkcan Akpinar, Regan J. Thomson^*

^*Corresponding author for this work

Chemistry

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

25 Scopus citations

Abstract

Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.

Original language	English (US)
Pages (from-to)	635-637
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2012.11.135
State	Published - Feb 13 2013

Keywords

Etherification
Maoecrystal V
Oxy-1,4-addition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.11.135

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title = "Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal v",

abstract = "Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.",

keywords = "Etherification, Maoecrystal V, Oxy-1,4-addition",

author = "Lazarski, {Kiel E.} and Berkcan Akpinar and Thomson, {Regan J.}",

note = "Funding Information: We gratefully acknowledge support from Northwestern University, the NIH (training grant T32AG000260 ), and the American Cancer Society by way of an Illinois Division Research Scholar Award (RSG-12-253-01-CDD) to R.J.T. and an institutional grant ( ACS-IRG 93-037-15 ) to the Robert H. Lurie Comprehensive Cancer Center at NU. B.A. is a Lambert Fellow within the Chemistry of Life Processes Institute at NU. ",

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AU - Lazarski, Kiel E.

AU - Akpinar, Berkcan

AU - Thomson, Regan J.

N1 - Funding Information: We gratefully acknowledge support from Northwestern University, the NIH (training grant T32AG000260 ), and the American Cancer Society by way of an Illinois Division Research Scholar Award (RSG-12-253-01-CDD) to R.J.T. and an institutional grant ( ACS-IRG 93-037-15 ) to the Robert H. Lurie Comprehensive Cancer Center at NU. B.A. is a Lambert Fellow within the Chemistry of Life Processes Institute at NU.

PY - 2013/2/13

Y1 - 2013/2/13

N2 - Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.

AB - Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.

KW - Etherification

KW - Maoecrystal V

KW - Oxy-1,4-addition

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Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal v

Abstract

Keywords

ASJC Scopus subject areas

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