Synthesis of 3-hexahelicenol and its transformation to 3-hexahelicenylamines,diphenylphosphine, methyl carboxylate,and dimethylthiocarbamate |
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| Authors: | Teplý Filip Stará Irena G Starý Ivo Kollárovic Adrian Saman David Vyskocil Stepán Fiedler Pavel |
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| Institution: | Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám 2, 166 10 Prague 6, Czech Republic. |
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| Abstract: | A nonphotochemical synthetic route to 3-hexahelicenol is reported. It involves a key 2+2+2] cycloisomerization of CH(3)O-substituted triyne that is readily available from 1-methoxy-3-methylbenzene and 1-bromo-2-(bromomethyl)naphthalene. Further functional group transformations led to 3-CO(2)CH(3), 3-NH(2), 3-PPh(2), and 3-SC(O)N(CH(3))(2) substituted hexahelicenes. |
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