Synthetic studies toward clavilactone A: A concise access to,-substituted -butenolides by metathesis

Hiroyuki Yasui, Shun Yamamoto, Ken ichi Takao, Kin ichi Tadano

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15 Citations (Scopus)

Abstract

Synthetic studies toward clavilactone A (1), using olefin metathesis as key steps, have been described. The ring-opening/ring-closing metathesis of 3bromo-2-[1-(1-cyclobutenyl)carboxyl-2-propenyl]-1,4-dimethoxybenzene (9) constructed a -arylated butenoiide (11). The ring-opening/ring-closing/cross metathesis of 2-[1-(1-cyclobutenyl)carboxyl-2-propenyl-1,4-dimethoxybenzene (19) in the presence of methallyl acetate (20) provided-2-(4-((E)-5-acetoxy- 4-methyl-3-pentenyl)-5-oxo-2,5-dihydrofuran-2-yl]-1,4-dimethoxybenzene (21). The π-allyl palladium complex-mediated intramolecular cyclization of 21 for construction of the 11-membered lactone moiety in the clavilactones was also explored.

Original languageEnglish
Pages (from-to)135-141
Number of pages7
JournalHeterocycles
Volume70
Publication statusPublished - 2006 Dec 31

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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