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Synthesis of the 1-Phenethyltetrahydroisoquinoline Alkaloids (+)-Dysoxyline, (+)-Colchiethanamine, and (+)-Colchiethine

  作者 REDDY RAJU JANNAPU; KAWAI NOBUYUKI; UENISHI JUNICHI  
  选自 期刊  Journal of Organic Chemistry;  卷期  2012年77-24;  页码  11101-11108  
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[摘要]Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids (+)-dysoxyline (1), (+)-colchiethanamine (2), and (+)-colchiethine (3) are described. In the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline with aromatic aldehydes, performed by using the Julia-Kocienski reaction, afforded the corresponding 1(beta-styryl)-substituted tetrahydroisoquinolines with complete retention of the absolute configuration at the C1 carbon atom. Functionalization of the products generated in these processes by using four- or five-step sequences gave the target alkaloids 1-3.

 
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