Diastereoselective One-Pot Synthesis of 7-and 8-Substituted 5-Phenylmorphans

被引：3

作者：

Lim, Hwan Jung ^{[1
,2
]}

Deschamps, Jeffrey R. ^{[3
]}

Jacobson, Arthur E. ^{[1
,2
]}

Rice, Kenner C. ^{[1
,2
]}

机构：

[1] NIDA, Drug Design & Synth Sect, Rockville, MD 20852 USA

[2] NIAAA, NIH, DHHS, Rockville, MD 20852 USA

[3] USN, Ctr Bimol Sci & Engn, Res Lab, Washington, DC 20375 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 19期

关键词：

RECEPTOR-MEDIATED PHENOMENA; AGONIST DELTA-ANTAGONIST; PROBES; MORPHINE;

D O I：

10.1021/ol2021862

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel 7- and 8-alkyl and aryl substituted 5-phenylmorphans were synthesized from substituted allyl halides and N-benzy1-4-ary1-1,2,3,6-tetrahydropyridine by a highly efficient and diastereoselective reaction series, "one-pot" alkylation and ene-imine cyclization followed by sodium borohydride reduction. Mild cyclization conditions gave the desired substituted 5-phenylmorphans in good yield as a single diastereomer.

引用

页码：5322 / 5325

页数：4

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