Synthesis of 3-Hexahelicenol and Its Transformation to 3-Hexahelicenylamines, Diphenylphosphine, Methyl Carboxylate, and Dimethylthiocarbamate
The Journal of Organic Chemistry2003Vol. 68(13), pp. 5193–5197
Citations Over TimeTop 10% of 2003 papers
Filip Teplý, Irena G. Stará̈, Ivo Starý, Adrian Kollárovič, David Šaman, Štěpán Vyskočil, Pavel Fiedler
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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