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KMID : 0043320110340081269
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Archives of Pharmacal Research
2011 Volume.34 No. 8 p.1269 ~ p.1276
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Stereoselective total synthesis of (+)-licochalcone E
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Liu Zhiguo
Wang Zengtao
Yoon Goo
Cheon Seung-Hoon
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Abstract
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The synthesis of (+)-licochalcone E (1) was accomplished for the first time in 13 steps from aryl bromide (6) with 8% overall yield. Palladium-catalyzed Negishi-Reformatsky coupling reaction of compound 6 with ethyl 2-(tributylstannyl)acetate provided the aryl acetic ester (5), which was converted to aryl acetamide (4) via mixed anhydride formation. Chiral auxiliarymediated methylation of the (S)-4-benzyl-2-oxazolidinone-derived aryl acetamide (4) provided the key asymmetric benzylic methyl group in compound 1.
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KEYWORD
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(+)-Licochalcone E, Negishi-Reformatsky reaction, Retrochalcone
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