A Two-Step, Stereoselective Synthesis of Nine- and Ten-Membered Carbocycles from Phthalates

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2015_sardina_orglett_stereoselective_synthesis.pdf (309.66 KB)
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URI: http://hdl.handle.net/10347/16987
ISSN: 1523-7060
E-ISSN: 1523-7052
DOI: 10.1021/acs.orglett.5b00552

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2015

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American Chemical Society
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A two-step, stereoselective procedure for the synthesis of nine- and ten-membered carbocycles from readily available phthalates is described. A variety of dialkyl phthalates have been transformed into [6,n]-fused bicyclo systems (n = 5, 6, 7) by a dearomatization/cyclization process and then converted into cyclonona- and cyclodecadienes through a bond cleavage reaction, whereby both processes are promoted by alkaline metals in THF

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Prado, G., Veiga, A., Fernández-Nieto, F., Paleo, M., & Sardina, F. (2015). A Two-Step, Stereoselective Synthesis of Nine- and Ten-Membered Carbocycles from Phthalates. Org. Lett., 17(9), 2054-2057. doi: 10.1021/acs.orglett.5b00552

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This work was supported by the Spanish MINECO (CTQ2011-22436), and the Xunta de Galicia (GRC2014/029)

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© 2015 American Chemical Society

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Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica