DIASTEREOCONTROLLED SYNTHESIS OF FUNCTIONALIZED TRANS-DECALINS VIA ELECTROCYCLIC REACTION OF TRIENOL ETHERS

Article abstract of DOI:10.1016/S0040-4039(00)94488-5

(E)-Trienol silyl ethers 10 and 11, selectively prepared by mono-Grignard reaction on methyl β-cyclogeranate (7) or by deprotonation of enone 8 were transformed to trans-decalins 5 and 6 by a thermal electrocyclic reaction.The hithero unknown enones 5 and 6 exhibit interesting organoleptic properties and show promise as versatile synthetic intermediates.The herein described transformation opens a new route for the direct construction of C(6)-functionalized drimanes such as cinnamodial (3) and forskolin (4).