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

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

Research output: Contribution to journalArticle

14 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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Cyclization
Palladium
Alkenes
Lactones
Acetates
1,4-dimethoxybenzene
clavilactone A
2,5-dihydrofuran

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic studies toward clavilactone A : A concise access to,-substituted -butenolides by metathesis. / Yasui, Hiroyuki; Yamamoto, Shun; Takao, Kenichi; Tadano, Kin ichi.

In: Heterocycles, Vol. 70, 31.12.2006, p. 135-141.

Research output: Contribution to journalArticle

Yasui, Hiroyuki ; Yamamoto, Shun ; Takao, Kenichi ; Tadano, Kin ichi. / Synthetic studies toward clavilactone A : A concise access to,-substituted -butenolides by metathesis. In: Heterocycles. 2006 ; Vol. 70. pp. 135-141.
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