Total Synthesis of the Proposed Structure of Tyloindane and Its Diastereoisomer

Abstract

AbstractIt is intriguing that tyloindane, which was isolated together with phenanthroindolizidine alkaloids, contains no nitrogen atom. Attracted by its unique structure and uncovered biological activity, we synthesized the proposed structure of tyloindane and its diastereoisomer. To achieve this goal, several strategies that include an aryl/alkene oxidative coupling, radical cyclization, and intramolecular Parham alkylation, were explored. The 1H NMR data of the synthesized compounds do not match those of the isolated sample (tyloindane), indicating that the structure of tyloindane should be reassigned.