Total Synthesis of the Antitumor-Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer

Glenn A. Pullella, Daniel Vuong, Ernest Lacey, Matthew J. Piggott

Research output: Contribution to journalArticle

Abstract

The 2,6′-bijuglone natural product diospyrin and its unnatural 3,6′-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.

Original languageEnglish
Pages (from-to)3623-3634
Number of pages12
JournalJournal of Natural Products
Volume83
Issue number12
DOIs
Publication statusPublished - 24 Dec 2020

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