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Synthesis 2022; 54(07): 1850-1856
DOI: 10.1055/a-1633-8333
DOI: 10.1055/a-1633-8333
paper
Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A
Financial support was provided by the Thailand Research Fund (DBG5480018) and the Royal Golden Jubilee Advanced Program (RAP61K0005) under the Thailand Research Fund. Additional financial support was provided by the Kasetsart University Research and Development Institute (KURDI), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Ministry of Higher Education, Science, Research and Innovation, Thailand, and the Department of Chemistry, Faculty of Science, Kasetsart University.
Abstract
Melotenine A, isolated from Melodinus tenuicaudatus, possesses significant anticancer activity against several human cancer cell lines. The synthesis of (±)-melotenine A was achieved without the use of any protecting groups in 11 steps with an overall yield of 6.7%. The key steps of our strategy were a Diels–Alder reaction to construct the tetracyclic framework and ring-closing metathesis to form the seven-membered ring of (±)-melotenine A.
Key words
natural product synthesis - melotenine A - anticancer agent - Diels–Alder reaction - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1633-8333.
- Supporting Information
Publication History
Received: 06 August 2021
Accepted after revision: 03 September 2021
Accepted Manuscript online:
03 September 2021
Article published online:
12 October 2021
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