Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues

Matthew L. Meketa; Steven M. Weinreb; Yoichi Nakao; Nobuhiro Fusetani

doi:10.1021/jo0707232

Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues

Matthew L. Meketa, Steven M. Weinreb, Yoichi Nakao, Nobuhiro Fusetani

Chemistry

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

42 Scopus citations

Abstract

(Chemical Equation Presented) A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described.

Original language	English (US)
Pages (from-to)	4892-4899
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	72
Issue number	13
DOIs	https://doi.org/10.1021/jo0707232
State	Published - Jun 22 2007

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo0707232

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abstract = "(Chemical Equation Presented) A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described.",

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Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues. / Meketa, Matthew L.; Weinreb, Steven M.; Nakao, Yoichi et al.
In: Journal of Organic Chemistry, Vol. 72, No. 13, 22.06.2007, p. 4892-4899.

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

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AU - Weinreb, Steven M.

AU - Nakao, Yoichi

AU - Fusetani, Nobuhiro

PY - 2007/6/22

Y1 - 2007/6/22

N2 - (Chemical Equation Presented) A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described.

AB - (Chemical Equation Presented) A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described.

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Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues

Abstract

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