Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans

Akio Ojida, Fumiyo Tanoue, Ken Kanematsu

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels–Alder reaction of benzofuranquinone 5 and Danishefsky diene 4. The Diels–Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.

Original languageEnglish
Pages (from-to)5970-5976
Number of pages7
JournalJournal of Organic Chemistry
Volume59
Issue number20
DOIs
Publication statusPublished - Oct 1 1994

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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