A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization

Matthew L. Meketa; Steven M. Weinreb

doi:10.1016/j.tet.2007.06.089

A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization

Matthew L. Meketa
, Steven M. Weinreb

Chemistry

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

25 Scopus citations

Abstract

A second generation total synthesis of the marine sponge metabolite ageladine A utilizing a biogenetically inspired 6π-2-azaelectrocyclization of triene 34 as the key step is performed to construct the imidazopyridine core of the metabolite.

Original language	English (US)
Pages (from-to)	9112-9119
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2007.06.089
State	Published - Sep 10 2007

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.06.089

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title = "A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization",

abstract = "A second generation total synthesis of the marine sponge metabolite ageladine A utilizing a biogenetically inspired 6π-2-azaelectrocyclization of triene 34 as the key step is performed to construct the imidazopyridine core of the metabolite.",

author = "Meketa, \{Matthew L.\} and Weinreb, \{Steven M.\}",

note = "Funding Information: We gratefully acknowledge financial support from the National Science Foundation (CHE-0404792). We also wish to thank Dr. H. Yennawar (Penn State Small Molecule X-ray Cystallographic Facility) for the X-ray determination of dibromopyrrole 31 , as well as Professor Blake Peterson and Jocelyn Edathil for assistance with reverse phase HPLC analysis. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

year = "2007",

month = sep,

day = "10",

doi = "10.1016/j.tet.2007.06.089",

language = "English (US)",

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AU - Meketa, Matthew L.

AU - Weinreb, Steven M.

N1 - Funding Information: We gratefully acknowledge financial support from the National Science Foundation (CHE-0404792). We also wish to thank Dr. H. Yennawar (Penn State Small Molecule X-ray Cystallographic Facility) for the X-ray determination of dibromopyrrole 31 , as well as Professor Blake Peterson and Jocelyn Edathil for assistance with reverse phase HPLC analysis. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

PY - 2007/9/10

Y1 - 2007/9/10

N2 - A second generation total synthesis of the marine sponge metabolite ageladine A utilizing a biogenetically inspired 6π-2-azaelectrocyclization of triene 34 as the key step is performed to construct the imidazopyridine core of the metabolite.

AB - A second generation total synthesis of the marine sponge metabolite ageladine A utilizing a biogenetically inspired 6π-2-azaelectrocyclization of triene 34 as the key step is performed to construct the imidazopyridine core of the metabolite.

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U2 - 10.1016/j.tet.2007.06.089

DO - 10.1016/j.tet.2007.06.089

M3 - Article

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SN - 0040-4020

VL - 63

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JF - Tetrahedron

IS - 37

ER -

A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization

Abstract

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