Regioselective Pd-catalyzed synthesis and application of 3-methyl-5-bromo-2-pyrone toward keto-phomactin A.
[Structure: see text] 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.
Ryu
Kimoon
K
Department of Chemistry, Hanyang University, Seoul, Korea 133-791.
Cho
Young-Suk
YS
Jung
Soo-Im
SI
Cho
Cheon-Gyu
CG
D000535:Aluminum / Q000737:chemistry; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*
C519349:3-methyl-5-bromo-2-pyrone; D006576:Heterocyclic Compounds, 4 or More Rings; D009942:Organometallic Compounds; D011753:Pyrones; C413206:phomactin A; D010165:Palladium; D000535:Aluminum