Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A

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 st...

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Veröffentlicht in:Synthesis (Stuttgart) 2022-04, Vol.54 (7), p.1850-1856
Hauptverfasser: Thanetchaiyakup, Adisak, Rattanarat, Hassayaporn, Aree, Sudaporn, Duangthongyou, Tanwawan, Nanok, Tanin, Chuanopparat, Nutthawat, Ngernmeesri, Paiboon
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Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1633-8333