Synthesis of 3-Hexahelicenol and Its Transformation to 3-Hexahelicenylamines, Diphenylphosphine, Methyl Carboxylate, and Dimethylthiocarbamate

Synthesis of 3-Hexahelicenol and Its Transformation to 3-Hexahelicenylamines, Diphenylphosphine, Methyl Carboxylate, and Dimethylthiocarbamate

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,...

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Veröffentlicht in:Journal of organic chemistry 2003-06, Vol.68 (13), p.5193-5197
Hauptverfasser: Teplý, Filip, Stará, Irena G, Starý, Ivo, Kollárovič, Adrian, Šaman, David, Vyskočil, Štěpán, Fiedler, Pavel
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034369t