Total Synthesis of Kanamienamide and Clarification of Biological Activity

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Abstract

The total synthesis of kanamienamide, an enamide with an enol ether and an 11-membered macrolactone of marine origin, was achieved. The synthesis features the construction of an enamide adjacent to an enol ether by Buchwald amidation and an 11-membered ring by Mitsunobu lactonization. In addition, on the basis of the biological assay of synthetic 1, we clarified that kanamienamide (1) was not an apoptosis-like cell death inducer, as reported in the isolation paper, and revealed its real biological activity as a necrosis-like cell death inducer.

Original languageEnglish
Pages (from-to)12503-12510
Number of pages8
JournalJournal of Organic Chemistry
Volume82
Issue number23
DOIs
Publication statusPublished - 2017 Dec 1

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Cell death
Bioactivity
Ether
Assays
Apoptosis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total Synthesis of Kanamienamide and Clarification of Biological Activity. / Ojima, Daisuke; Iwasaki, Arihiro; Suenaga, Kiyotake.

In: Journal of Organic Chemistry, Vol. 82, No. 23, 01.12.2017, p. 12503-12510.

Research output: Contribution to journalArticle

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