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Synthesis of 2-pyrones bridged at the 3- and 6-positions by ring-closing metathesis

Heterocycles, ISSN: 0385-5414, Vol: 65, Issue: 5, Page: 1167-1176
2005
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Article Description

Synthesis of 4-hydroxy-2-pyrones bridged at the 3- and 6-positions by ring-closing metathesis was studied. The reaction of 6-(9-decenyl)-4-methoxy-3- (10-undecenoyl)pyran-2-one (6b) by the first generation ruthenium catalyst (7) gave 3,6-bridged 2-pyrone (10b) in 62% yield. The reaction of 3-(6-heptenoyl)-6-(5-hexenyl)-4-methoxypyran-2-one (6a) (n = 4) under the same conditions afforded the 3,6-bridged 2-pyrone (10a) in 6% yield together with considerable amounts of intermolecular metathesis products.

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