A Concise Total Synthesis of Dictyodendrins F, H, and i Using Aryl Ynol Ethers as Key Building Blocks

Wenhan Zhang, Joseph M. Ready

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

We report a concise total synthesis of dictyodendrin F and the first total syntheses of dictyodendrins H and I in six steps. In these syntheses, aryl ynol ethers were employed as the key building blocks to introduce aryl and heteroaryl rings in the dictyodendrins. This rapid synthesis utilized a novel hetero-[2 + 2]-cycloaddition reaction between two aryl ynol ethers to yield a cyclobutenone ring. The cyclobutenone was sequentially converted into a highly substituted carbazole via a retro-4π/6π-electrocyclization-N-acylation cascade reaction to provide the dictyodendrin core. Consecutive intramolecular oxidative coupling and deprotection gave dictyodendrins F, H, and I.

Original languageEnglish (US)
Pages (from-to)10684-10692
Number of pages9
JournalJournal of the American Chemical Society
Volume138
Issue number33
DOIs
StatePublished - Aug 24 2016

Fingerprint

Ethers
Oxidative Coupling
Acylation
Cycloaddition Reaction
Cycloaddition
cyclobutenone
dictyodendrins F
carbazole

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Chemistry(all)
  • Colloid and Surface Chemistry

Cite this

A Concise Total Synthesis of Dictyodendrins F, H, and i Using Aryl Ynol Ethers as Key Building Blocks. / Zhang, Wenhan; Ready, Joseph M.

In: Journal of the American Chemical Society, Vol. 138, No. 33, 24.08.2016, p. 10684-10692.

Research output: Contribution to journalArticle

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