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

44 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

UN SDGs

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

SDG 14 Life Below Water

All Science Journal Classification (ASJC) codes

Organic Chemistry

Access to Document

10.1021/jo0707232

Cite this

@article{ad18bc60288f4e3ba79b844f337e216b,

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 (US)",

volume = "72",

pages = "4892--4899",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

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

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 - https://www.scopus.com/pages/publications/34250898546

UR - https://www.scopus.com/pages/publications/34250898546#tab=citedBy

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 -

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

UN SDGs

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this