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Volumn 624, Issue 1-2, 2001, Pages 316-326

A short synthesis of (-)-dendrobine. Some observations on the nickel mediated radical cyclisation and on the Pauson-Khand reaction

Author keywords

( ) Dendrobine; Nickel metal; Nitrogen centred radical; Pauson Khand reaction; Radical cyclisation; Total synthesis

Indexed keywords


EID: 0000141413     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)00662-3     Document Type: Article
Times cited : (48)

References (55)
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    • 0034686072 scopus 로고    scopus 로고
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    • As shown in Scheme 9 below, the penultimate intermediate in the Pauson-Khand reaction can undergo the normal reductive elimination to give cyclopentenone 26 or a β-elimination to give 27, perhaps assisted by complexation of the basic nitrogen to a cobalt atom. This hypothesis is supported by similar observations on zirconium-mediated [2 + 2 + 1] cycloadditions of related benzylamines: Ref. [6d] and J. Barluenga, R. Sanz, F. Fananas, Chem. Eur. J. 3 (1997) 1324-1336.
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    • Without protection of the hydroxy group, the Pauson-Khand reaction proved very sluggish (19% yield) and was accompanied by a large amount of demetallated product (55% yield). For related observations, see: C. Mukai, J.S. Kim, M. Uchiyama, M. Hanaoka, Tetrahedron Lett. 39 (1998) 7909-7912.
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