Total Synthesis of the Proposed Structure of Tyloindane and Its Diastereoisomer

Dedicated to the 100th anniversary of Chemistry at Nankai University

Abstract

It 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.

Key words

tyloindane - phenanthroindolizidine alkaloids - oxidative coupling - total synthesis - natural products

Publication History

Received: 21 November 2021

Accepted after revision: 08 December 2021

Article published online:
26 January 2022

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