TY - JOUR
T1 - Synthetic studies toward clavilactone A
T2 - A concise access to,-substituted -butenolides by metathesis
AU - Yasui, Hiroyuki
AU - Yamamoto, Shun
AU - Takao, Ken ichi
AU - Tadano, Kin ichi
PY - 2006/12/31
Y1 - 2006/12/31
N2 - 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.
AB - 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.
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U2 - 10.3987/com-06-s(w)42
DO - 10.3987/com-06-s(w)42
M3 - Article
AN - SCOPUS:33947703219
SN - 0385-5414
VL - 70
SP - 135
EP - 141
JO - Heterocycles
JF - Heterocycles
ER -