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| DC Field | Value | Language |
|---|
| contributor.author | Sarkar, T K | - |
| contributor.author | Hazra, A | - |
| contributor.author | Gangopadhyay, P | - |
| contributor.author | Panda, Niranjan | - |
| contributor.author | Slanina, Z | - |
| contributor.author | Chun-Cheng, Lin | - |
| contributor.author | Hui-Ting, Chen | - |
| date.accessioned | 2007-09-30T10:13:19Z | - |
| date.available | 2007-09-30T10:13:19Z | - |
| date.issued | 2005 | - |
| identifier.citation | Tetrahedron, Vol 61, Iss 5, P 1155-1165 | en |
| identifier.uri | http://dx.doi.org/10.1016/j.tet.2004.11.046 | - |
| identifier.uri | http://hdl.handle.net/2080/516 | - |
| description | Copyright for the published version belongs to Elsevier | en |
| description.abstract | An aza-ene reaction has been used for the first time for the synthesis of two 5-membered lactam-hydrazides, each with a built-in allylsilane terminator for further elaboration. One of the lactam-hydrazides was transformed via an allylsilane-hydrazonium ion ring closure to a fused tetrahydropyrazole which may be considered as a mono-nitrogen analog of the biologically significant necine bases. A density functional theoretical study (B3LYP/6-21G*) was undertaken to provide insight into the factors that favor a synclinal transition structure of the hydrazonium ion intermediate leading to the tetrahydropyrazole. This stereocontrolled synthesis served as a model for the multi-step conversion of the other lactam-hydrazide, the substituted 2-pyrrolidinone, to necine bases (±)-supinidine and (±)-macronecine. An allylsilane-aldehyde ring closure formed the key step in the synthesis of these natural products. | en |
| format.extent | 1013818 bytes | - |
| format.mimetype | application/pdf | - |
| language.iso | en | - |
| publisher | Elsevier | en |
| subject | Aza-ene reaction | en |
| subject | Heterocyclic allylsilanes | en |
| subject | Fused tetrahydropyrazole | en |
| subject | Necine bases | en |
| subject | Supinidine | en |
| subject | Macronecine | en |
| title | Synthesis of the necine bases (±)-macronecine and (±)-supinidine via an aza-ene reaction and allylsilane induced ring closure | en |
| type | Article | en |
| Appears in Collections: | Journal Articles
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| niranjan1.pdf | | 990Kb | Adobe PDF | View/Open |
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