A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine Alkaloid Gilbertine

Fei Tang; Martin G. Banwell; Anthony C. Willis

doi:10.1021/acs.joc.6b01424

A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine Alkaloid Gilbertine

Fei Tang, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Reductive cyclization of the 2,4,5-trisubstituted cyclohexenone 16 using dihydogen in the presence of Raney cobalt afforded compound 17 (60%) that could be elaborated over a further five steps, including one involving a cationic cyclization process, into the racemic modification of the unusual uleine alkaloid gilbertine. Single-crystal X-ray analyses of compounds (±)-1, 16, and a derivative of 17 are reported.

Original language	English
Pages (from-to)	10551-10557
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	81
Issue number	21
DOIs	https://doi.org/10.1021/acs.joc.6b01424
Publication status	Published - 4 Nov 2016

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10.1021/acs.joc.6b01424

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abstract = "Reductive cyclization of the 2,4,5-trisubstituted cyclohexenone 16 using dihydogen in the presence of Raney cobalt afforded compound 17 (60%) that could be elaborated over a further five steps, including one involving a cationic cyclization process, into the racemic modification of the unusual uleine alkaloid gilbertine. Single-crystal X-ray analyses of compounds (±)-1, 16, and a derivative of 17 are reported.",

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AU - Willis, Anthony C.

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N2 - Reductive cyclization of the 2,4,5-trisubstituted cyclohexenone 16 using dihydogen in the presence of Raney cobalt afforded compound 17 (60%) that could be elaborated over a further five steps, including one involving a cationic cyclization process, into the racemic modification of the unusual uleine alkaloid gilbertine. Single-crystal X-ray analyses of compounds (±)-1, 16, and a derivative of 17 are reported.

AB - Reductive cyclization of the 2,4,5-trisubstituted cyclohexenone 16 using dihydogen in the presence of Raney cobalt afforded compound 17 (60%) that could be elaborated over a further five steps, including one involving a cationic cyclization process, into the racemic modification of the unusual uleine alkaloid gilbertine. Single-crystal X-ray analyses of compounds (±)-1, 16, and a derivative of 17 are reported.

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JF - Journal of Organic Chemistry

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A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine Alkaloid Gilbertine

Abstract

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