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Please use this identifier to cite or link to this item: http://hdl.handle.net/2080/516

Title: Synthesis of the necine bases (±)-macronecine and (±)-supinidine via an aza-ene reaction and allylsilane induced ring closure
Authors: Sarkar, T K
Hazra, A
Gangopadhyay, P
Panda, Niranjan
Slanina, Z
Chun-Cheng, Lin
Hui-Ting, Chen
Keywords: Aza-ene reaction
Heterocyclic allylsilanes
Fused tetrahydropyrazole
Necine bases
Supinidine
Macronecine
Issue Date: 2005
Publisher: Elsevier
Citation: Tetrahedron, Vol 61, Iss 5, P 1155-1165
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.
Description: Copyright for the published version belongs to Elsevier
URI: http://dx.doi.org/10.1016/j.tet.2004.11.046
http://hdl.handle.net/2080/516
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