Synthesis of 9-substituted tetrahydrodiazepinopurines - Asmarine A analogues

Doron Pappo; Yoel Kashman

doi:10.1016/S0040-4020(03)01058-5

Synthesis of 9-substituted tetrahydrodiazepinopurines - Asmarine A analogues

Doron Pappo, Yoel Kashman^*

^*Corresponding author for this work

School of Chemistry

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

Abstract

Asmarines are marine alkaloids, with a unique tetrahydro[1,4]diazepino-[1,2,3-g,h]purine (THDAP) structure and interesting biological properties. Three synthetic approaches were employed for the preparation of the THDAP system. Several N-9, of the purine, protecting groups were investigated. ¹⁵N-Chemical shifts measured from ¹⁵NH HMBC experiments for several compounds, that demonstrate the influence of various structural features on the ¹⁵N-resonances are reported.

Original language	English
Pages (from-to)	6493-6501
Number of pages	9
Journal	Tetrahedron
Volume	59
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4020(03)01058-5
State	Published - 18 Aug 2003

Keywords

Asmarine
Diazepinopurine
Mitsunobu reaction
N resonances
NH HMBC
Purine

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

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10.1016/S0040-4020(03)01058-5

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abstract = "Asmarines are marine alkaloids, with a unique tetrahydro[1,4]diazepino-[1,2,3-g,h]purine (THDAP) structure and interesting biological properties. Three synthetic approaches were employed for the preparation of the THDAP system. Several N-9, of the purine, protecting groups were investigated. 15N-Chemical shifts measured from 15NH HMBC experiments for several compounds, that demonstrate the influence of various structural features on the 15N-resonances are reported.",

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AU - Pappo, Doron

AU - Kashman, Yoel

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N2 - Asmarines are marine alkaloids, with a unique tetrahydro[1,4]diazepino-[1,2,3-g,h]purine (THDAP) structure and interesting biological properties. Three synthetic approaches were employed for the preparation of the THDAP system. Several N-9, of the purine, protecting groups were investigated. 15N-Chemical shifts measured from 15NH HMBC experiments for several compounds, that demonstrate the influence of various structural features on the 15N-resonances are reported.

AB - Asmarines are marine alkaloids, with a unique tetrahydro[1,4]diazepino-[1,2,3-g,h]purine (THDAP) structure and interesting biological properties. Three synthetic approaches were employed for the preparation of the THDAP system. Several N-9, of the purine, protecting groups were investigated. 15N-Chemical shifts measured from 15NH HMBC experiments for several compounds, that demonstrate the influence of various structural features on the 15N-resonances are reported.

KW - Asmarine

KW - Diazepinopurine

KW - Mitsunobu reaction

KW - N resonances

KW - NH HMBC

KW - Purine

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VL - 59

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EP - 6501

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Synthesis of 9-substituted tetrahydrodiazepinopurines - Asmarine A analogues

Abstract

Keywords

UN SDGs

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