Synthesis of 3-hexahelicenol and its transformation to 3-hexahelicenylamines, diphenylphosphine, methyl carboxylate, and dimethylthiocarbamate

Filip Teplý; Irena G Stará; Ivo Starý; Adrian Kollárovic; David Saman; Stepán Vyskocil; Pavel Fiedler

doi:10.1021/jo034369t

Synthesis of 3-hexahelicenol and its transformation to 3-hexahelicenylamines, diphenylphosphine, methyl carboxylate, and dimethylthiocarbamate

J Org Chem. 2003 Jun 27;68(13):5193-7. doi: 10.1021/jo034369t.

Authors

Filip Teplý¹, Irena G Stará, Ivo Starý, Adrian Kollárovic, David Saman, Stepán Vyskocil, Pavel Fiedler

Affiliation

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám 2, 166 10 Prague 6, Czech Republic.

PMID: 12816476
DOI: 10.1021/jo034369t

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.