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

共 50 条

[31] Highly Diastereoselective Synthesis of Fully Substituted Tetrahydrofurans by a One-Pot Cascade Reaction of Aryldiazoacetates with Allyl Alcohols
Xu, Xinfang
Han, Xingchun
Yang, Liping
Hu, Wenhao
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) : 12604 - 12607
[32] SYNTHESIS OF SOME 8-SUBSTITUTED 5-DEAZAFLAVINS
YONEDA, F
MORI, K
SAKUMA, Y
KOSHIRO, A
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (04) : 945 - 947
[33] SIMPLE ONE-POT THREE COMPONENT SYNTHESIS OF SYMMETRICALLY SUBSTITUTED 7,7′-BISINDOLIZINES
Teodorescu, Florina
Georgescu, Emilian
Georgescu, Florentina
Dumitrascu, Florea
Popa, Marcel Mirel
Draghici, Constantin
Nicolescu, Alina
Deleanu, Calin
REVUE ROUMAINE DE CHIMIE, 2018, 63 (7-8) : 737 - +
[34] Catalytic One-Pot Synthesis of 1-Substituted 5,6,7,8-Tetrahydroindolizine Derivatives
Biletzki, Tobias
Imhof, Wolfgang
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (33) : 6513 - 6516
[35] ONE-POT SYNTHESIS OF TRICHLOROMETHYL-SUBSTITUTED ALCOHOLS
BRUNNER, H
WIMMER, P
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 309 (1-2) : C4 - C6
[36] δ-Nitroalkanols as precursors for the one-pot synthesis of substituted tetrahydrofurans
Ballini, R
Fiorini, D
Gil, MV
Palmieri, A
Román, E
Serrano, JA
TETRAHEDRON LETTERS, 2003, 44 (14) : 2795 - 2797
[37] An efficient one-pot synthesis of 4′-substituted flavones
Wang, Xuejun
Liu, Jianli
Zhang, Yilin
Liang, Xuhua
CHEMICAL PAPERS, 2018, 72 (01) : 229 - 233
[38] One-Pot Synthesis of alpha-Substituted Acrylates
Matziari, Magdalini
Xie, Yixin
SYNOPEN, 2018, 2 (02): : 161 - 167
[39] Novel one-pot synthesis of symmetrically substituted ureas
Wu, Xingxing
Niu, Qingfen
Li, Tianduo
SYNTHETIC COMMUNICATIONS, 2016, 46 (16) : 1364 - 1369
[40] ONE-POT SYNTHESIS OF PERFLUOROBUTYL-SUBSTITUTED POLYSILYNE
WATANABE, A
ITO, O
MIWA, T
CHEMISTRY LETTERS, 1995, (09) : 757 - 758

← 1 2 3 4 5 →