Total synthesis of (±)-cyclooroidin

Gianluca Papeo; M. A G Z Frau; Daniela Borghi; Mario Varasi

doi:10.1016/j.tetlet.2005.10.060

Total synthesis of (±)-cyclooroidin

Gianluca Papeo, M. A G Z Frau, Daniela Borghi, Mario Varasi

Istituto Europeo di Oncologia

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

Abstract

The first total synthesis of (±)-cyclooroidin, a member of the pyrrole-imidazole alkaloid family recently isolated from the sponge Agelas oroides in optically pure form, is described. The synthesis was achieved in nine linear steps, with an overall yield of 10%. Key step was a Wolff bromoketone synthesis performed on the intermediate longamide B.

Original language	English
Pages (from-to)	8635-8638
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2005.10.060
Publication status	Published - Dec 12 2005

Keywords

Cyclooroidin
Pyrrole-imidazole alkaloids
Wolff bromoketone synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tetlet.2005.10.060

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title = "Total synthesis of (±)-cyclooroidin",

abstract = "The first total synthesis of (±)-cyclooroidin, a member of the pyrrole-imidazole alkaloid family recently isolated from the sponge Agelas oroides in optically pure form, is described. The synthesis was achieved in nine linear steps, with an overall yield of 10%. Key step was a Wolff bromoketone synthesis performed on the intermediate longamide B.",

keywords = "Cyclooroidin, Pyrrole-imidazole alkaloids, Wolff bromoketone synthesis",

author = "Gianluca Papeo and Frau, {M. A G Z} and Daniela Borghi and Mario Varasi",

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T1 - Total synthesis of (±)-cyclooroidin

AU - Papeo, Gianluca

AU - Frau, M. A G Z

AU - Borghi, Daniela

AU - Varasi, Mario

PY - 2005/12/12

Y1 - 2005/12/12

N2 - The first total synthesis of (±)-cyclooroidin, a member of the pyrrole-imidazole alkaloid family recently isolated from the sponge Agelas oroides in optically pure form, is described. The synthesis was achieved in nine linear steps, with an overall yield of 10%. Key step was a Wolff bromoketone synthesis performed on the intermediate longamide B.

AB - The first total synthesis of (±)-cyclooroidin, a member of the pyrrole-imidazole alkaloid family recently isolated from the sponge Agelas oroides in optically pure form, is described. The synthesis was achieved in nine linear steps, with an overall yield of 10%. Key step was a Wolff bromoketone synthesis performed on the intermediate longamide B.

KW - Cyclooroidin

KW - Pyrrole-imidazole alkaloids

KW - Wolff bromoketone synthesis

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DO - 10.1016/j.tetlet.2005.10.060

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

ER -

Total synthesis of (±)-cyclooroidin

Abstract

Keywords

ASJC Scopus subject areas

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