Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic

Byoung J. Min; Xuyuan Gu; Takashi Yamamoto; Ravil R. Petrov; Hongchang Qu; Yeon Sun Lee; Victor J Hruby

doi:10.1016/j.tetlet.2008.01.137

Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic

Byoung J. Min, Xuyuan Gu, Takashi Yamamoto, Ravil R. Petrov, Hongchang Qu, Yeon Sun Lee, Victor J Hruby

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

13 Scopus citations

Abstract

A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an N^α-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.

Original language	English (US)
Pages (from-to)	2316-2319
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2008.01.137
State	Published - Mar 31 2008

Keywords

Acetals
Internal bicyclic peptidomimetics
N-Acylimnium ion cyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.01.137

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title = "Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic",

abstract = "A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an Nα-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.",

keywords = "Acetals, Internal bicyclic peptidomimetics, N-Acylimnium ion cyclization",

author = "Min, {Byoung J.} and Xuyuan Gu and Takashi Yamamoto and Petrov, {Ravil R.} and Hongchang Qu and Lee, {Yeon Sun} and Hruby, {Victor J}",

note = "Funding Information: This work was supported by grants from US Public Health Service (DK 17420) and the National Institute on Drug Abuse (DA 06284 and DA 13449). We thank Professor Richard Glass and Professor Hamish Christie (The University of Arizona) for helpful discussions regarding the reaction mechanism. ",

year = "2008",

month = mar,

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doi = "10.1016/j.tetlet.2008.01.137",

language = "English (US)",

volume = "49",

pages = "2316--2319",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "14",

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T1 - Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic

AU - Min, Byoung J.

AU - Gu, Xuyuan

AU - Yamamoto, Takashi

AU - Petrov, Ravil R.

AU - Qu, Hongchang

AU - Lee, Yeon Sun

AU - Hruby, Victor J

N1 - Funding Information: This work was supported by grants from US Public Health Service (DK 17420) and the National Institute on Drug Abuse (DA 06284 and DA 13449). We thank Professor Richard Glass and Professor Hamish Christie (The University of Arizona) for helpful discussions regarding the reaction mechanism.

PY - 2008/3/31

Y1 - 2008/3/31

N2 - A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an Nα-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.

AB - A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an Nα-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.

KW - Acetals

KW - Internal bicyclic peptidomimetics

KW - N-Acylimnium ion cyclization

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DO - 10.1016/j.tetlet.2008.01.137

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JF - Tetrahedron Letters

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ER -

Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 639677: Experimental Crystal Structure Determination

Cite this

Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 639677: Experimental Crystal Structure Determination

Cite this