Regioselective Pd-Catalyzed Synthesis and Application of 3-Methyl-5-bromo-2-pyrone toward Keto-phomactin A

Regioselective Pd-Catalyzed Synthesis and Application of 3-Methyl-5-bromo-2-pyrone toward Keto-phomactin A

An efficient one-step synthetic protocol for 3-methyl-5-bromo-2-pyrone was developed using the C3-selective Pd-catalyzed coupling reaction of 3,5-dibromo-2-pyrone with Me3Al−dimethylaminoethanol complex. A subsequent seven-step reaction sequence provided a cyclohexenyl bromide, which served as the k...

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Veröffentlicht in:Organic letters 2006-07, Vol.8 (15), p.3343-3345
Hauptverfasser: Ryu, Kimoon, Cho, Young-Suk, Jung, Soo-Im, Cho, Cheon-Gyu
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Sprache:eng
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Aluminum - chemistry
Catalysis
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Pyrones - chemistry
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container_title Organic letters
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creator Ryu, Kimoon
Cho, Young-Suk
Jung, Soo-Im
Cho, Cheon-Gyu
description An efficient one-step synthetic protocol for 3-methyl-5-bromo-2-pyrone was developed using the C3-selective Pd-catalyzed coupling reaction of 3,5-dibromo-2-pyrone with Me3Al−dimethylaminoethanol complex. A subsequent seven-step reaction sequence provided a cyclohexenyl bromide, which served as the key intermediate for the synthesis of the keto analogue of phomactin A, in 31% overall yield.
doi_str_mv 10.1021/ol061231z
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subjects Aluminum - chemistry
Catalysis
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Pyrones - chemistry
title Regioselective Pd-Catalyzed Synthesis and Application of 3-Methyl-5-bromo-2-pyrone toward Keto-phomactin A
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