Synthesis of 3-Hexahelicenol and Its Transformation to 3-Hexahelicenylamines, Diphenylphosphine, Methyl Carboxylate, and Dimethylthiocarbamate
- 24 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (13) , 5193-5197
- https://doi.org/10.1021/jo034369t
Abstract
A nonphotochemical synthetic route to 3-hexahelicenol is reported. It involves a key [2+2+2] cycloisomerization of CH3O-substituted triyne that is readily available from 1-methoxy-3-methylbenzene and 1-bromo-2-(bromomethyl)naphthalene. Further functional group transformations led to 3-CO2CH3, 3-NH2, 3-PPh2, and 3-SC(O)N(CH3)2 substituted hexahelicenes.Keywords
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