Synthesis 2022; 54(08): 1983-1988
DOI: 10.1055/s-0037-1610789
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Total Synthesis of the Proposed Structure of Tyloindane and Its Diastereoisomer

Bo Su
a   College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
b   State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China
,
Hui Zhang
b   State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China
,
Qingmin Wang
b   State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China
› Author Affiliations
We are grateful to the National Natural Science Foundation of China (21732002, 22077071) and the Fundamental Research Funds for the Central Universities, Nankai University (735/63213083) for generous financial support for our programs.


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.

Supporting Information



Publication History

Received: 21 November 2021

Accepted after revision: 08 December 2021

Article published online:
26 January 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
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