Issue 10, 2020

Total synthesis and biological evaluation of simplified aplyronine analogues as synthetically tractable anticancer agents

Abstract

The aplyronines are a family of highly cytotoxic marine natural products with potential application in targeted cancer chemotherapy. To address the severe supply issue, function-oriented molecular editing of their macrolactone scaffold led to the design of a series of simplified aplyronine analogues. Enabled by a highly convergent aldol-based route, the total synthesis of four analogues was achieved, with a significant improvement in step economy versus previous compounds, and their cancer cell growth inhibition in the HeLa cell line was determined. The modular strategy presented offers a means for significantly shortening their chemical synthesis to facilitate the continued development of this promising class of anticancer agent.

Graphical abstract: Total synthesis and biological evaluation of simplified aplyronine analogues as synthetically tractable anticancer agents

Supplementary files

Article information

Article type
Communication
Submitted
20 Nov. 2019
Accepted
03 Janv. 2020
First published
03 Janv. 2020

Chem. Commun., 2020,56, 1529-1532

Total synthesis and biological evaluation of simplified aplyronine analogues as synthetically tractable anticancer agents

T. R. Pettigrew, R. J. Porter, S. J. Walsh, M. P. Housden, N. Y. S. Lam, J. S. Carroll, J. S. Parker, D. R. Spring and I. Paterson, Chem. Commun., 2020, 56, 1529 DOI: 10.1039/C9CC09050A

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