Regioselective Pd-catalyzed synthesis and application of 3-methyl-5-bromo-2-pyrone toward keto-phomactin A

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초록

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.

키워드

CROSS-COUPLING REACTIONENANTIOSELECTIVE SYNTHESISTRICYCLIC FURANOCHROMANABSOLUTE-CONFIGURATIONCOREMETHYLATIONANTAGONISTSCOCKROACHHALIDES
제목
Regioselective Pd-catalyzed synthesis and application of 3-methyl-5-bromo-2-pyrone toward keto-phomactin A
저자
Ryu, KimoonCho, Young-SukJung, Soo-ImCho, Cheon-Gyu
DOI
10.1021/ol061231z
발행일
2006-07
유형
Article
저널명
Organic Letters
8
15
페이지
3343 ~ 3345