Tandem intermolecular alkylation-intramolecular robinson annelation: A novel and stereoselective construction of the octalin skeleton - Expeditious synthesis of (-)-tanabalin

Article abstract of DOI:10.1016/S0040-4039(99)00198-7

Tanabalin (1), an insect antifeedant, was synthesized in optically active form employing a known δ-lactone (F) as the only source of chirality. The key step is a tandem intermolecular alkylation-intramolecular Robinson annelation to construct the trans-octalin skeleton.