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

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

42 被引用数 (Scopus)

抄録

(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.

本文言語	English
ページ（範囲）	4892-4899
ページ数	8
ジャーナル	Journal of Organic Chemistry
巻	72
号	13
DOI	https://doi.org/10.1021/jo0707232
出版ステータス	Published - 2007 6月 22

ASJC Scopus subject areas

有機化学

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

文献へのアクセス

10.1021/jo0707232

他のファイルとリンク

フィンガープリント

「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」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{5d01433d9c2e46008835addc0a417e3b,

title = "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 = "(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.",

author = "Meketa, {Matthew L.} and Weinreb, {Steven M.} and Yoichi Nakao and Nobuhiro Fusetani",

year = "2007",

month = jun,

day = "22",

doi = "10.1021/jo0707232",

language = "English",

volume = "72",

pages = "4892--4899",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - 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

AU - Meketa, Matthew L.

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.

UR - http://www.scopus.com/inward/record.url?scp=34250898546&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34250898546&partnerID=8YFLogxK

U2 - 10.1021/jo0707232

DO - 10.1021/jo0707232

M3 - Article

C2 - 17539689

AN - SCOPUS:34250898546

SN - 0022-3263

VL - 72

SP - 4892

EP - 4899

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -