A Synthetic Approach to (±)-Tridentoquinone

Roger F.C. Brown, Andrea J. Robinson

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Synthesis of the ansa-bridged benzofuranquinone (±)- tridentoquinone (±)-(1) is approached by construction of a C4 methyl ketone chain at the 3-position of 6-bromo-4, 5, 7-trimethoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran (10) and alkylation at its 6-position leading after modification to a dimethyl C10 aldehydic chain. Closure of the ansa bridge by McMurry coupling of the aldehyde and ketone groups of the intermediate (33) with C8K/TiCl3 appears to occur, but in poor yield and with uncertain stereochemistry, and the synthesis has not been completed.

Original languageEnglish
Pages (from-to)515-529
Number of pages15
JournalAustralian Journal of Chemistry
Issue number3
Publication statusPublished - 1 Jan 1995

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