Premium
Model Studies toward the Total Synthesis of Thebaine by an Intramolecular Cycloaddition Strategy
Author(s) -
Koukal Petr,
Hájíček Josef,
Gupta Setu,
Hudlický Tomáš
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701817
Subject(s) - cycloaddition , intramolecular force , thebaine , chemistry , benzofuran , intermolecular force , diene , thermal decomposition , combinatorial chemistry , organic chemistry , medicinal chemistry , computational chemistry , catalysis , molecule , biology , natural rubber , codeine , morphine , pharmacology
Three model compounds required for an approach to thebaine by intramolecular [4+2] cycloaddition were prepared. In the first two cases the anticipated cycloaddition products were obtained under thermal conditions. Thermolysis of the third, more advanced model compound, afforded products resulting from rearrangements and/or elimination. A study of analogous intra‐ and intermolecular reactions using benzofuran as dienophile and various electron‐poor and electron‐rich dienes (pyridazines, pyranones, Danishefsky diene) was undertaken.