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Communication | Special issue | Vol 70, No. 1, 2006, pp.135-141
Published online, 24th October, 2006
DOI: 10.3987/COM-06-S(W)42
Synthetic Studies toward Clavilactone A: A Concise Access to α,γ-Substituted γ-Butenolides by Metathesis

Hiroyuki Yasui, Shun Yamamoto, Ken-ichi Takao, and Kin-ichi Tadano*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan

Abstract

Synthetic studies toward clavilactone A (1), using olefin metathesis as key steps, have been described. The ring-opening/ring-closing metathesis of 3- bromo-2-[1-(1-cyclobutenyl)carboxyl-2-propenyl]-1,4-dimethoxybenzene (9) constructed a γ-arylated butenolide (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.