Synthesis of Tetrahydroisoquinoline Alkaloids via Anodic Cyanation as the Key Step

被引：56

作者：

Louafi, Fadila ^{[2
]}

Hurvois, Jean-Pierre ^{[1
]}

Chibani, Aissa ^{[2
]}

Roisnel, Thierry ^{[1
]}

机构：

[1] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France

[2] Univ Mentouri Constantine, Fac Sci Exactes, Dept Chim, Constantine 25000, Algeria

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 16期

关键词：

ASYMMETRIC-SYNTHESIS; ELECTROOXIDATIVE CYCLIZATION; ELECTROCHEMICAL OXIDATION; ENANTIOSPECIFIC SYNTHESIS; ELECTROORGANIC CHEMISTRY; ELECTRON-TRANSFER; ALKYLATION; AMINES; INDOLIZIDINE; PIPERIDINES;

D O I：

10.1021/jo100714y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a new route to tetrahydroisoquinoline (THIQ) alkaloids involving the alkylation of alpha-aminonitrile 2 as a key step. The latter compound was prepared by anodic cyanation of the corresponding tertiary amine 1. Reductive decyanation of alpha-aminonitriles 6a-c proceeded diastereoselectively (up to 95% de) to deliver the Cl-substituted alkaloids precursors 9a-c. The syntheses of (+/-)-carnegine, (+/-)-norlaudanosine, and (+/-)-O,O-dimethylcoclaurine have been achieved.

引用

页码：5721 / 5724

页数：4

共 60 条

[1] Enantioselective Formal Synthesis of (+)-Dihydrocorynantheine and (-)-Dihydrocorynantheol [J].

Amat, Mercedes ;

Gomez Esque, Arantxa ;

Escolano, Carmen ;

Santos, Maria M. M. ;

Molins, Elies ;

Bosch, Joan .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1205-1211

[2] NEW SYNTHESIS OF PIPECOLIC ACID AND ANALOGS [J].

ASHER, V ;

BECU, C ;

ANTEUNIS, MJO ;

CALLENS, R .

TETRAHEDRON LETTERS, 1981, 22 (02) :141-144

[3] Cyclization via carbolithiation of α-amino alkyllithium reagents [J].

Bahde, Robert J. ;

Rychnovsky, Scott D. .

ORGANIC LETTERS, 2008, 10 (18) :4017-4020

[4] EXTENT OF BOND FORMATION IN TRANSITION-STATE FOR ALKYLATION AT NITROGEN AND AT CARBON [J].

BARE, TM ;

HOUSE, HO ;

HERSHEY, ND ;

SWAIN, CG .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :997-&

[5]

BECKER JY, 1976, J ELECTROANAL CHEM, V68, P181, DOI 10.1016/0368-1874(76)80046-9

[6] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, KW .

NATURAL PRODUCT REPORTS, 2003, 20 (03) :342-365

[7] ELECTROSYNTHESIS IN A BEAKER - AN EFFICIENT ROUTE TO MORPHINANDIENONES AVOIDING POTENTIOSTATS FOR CONTROL OF ELECTRODE-POTENTIALS [J].

BENTLEY, TW ;

MORRIS, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :5005-5007

[8] Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles [J].

Bergner, Ines ;

Wiebe, Christine ;

Meyer, Nino ;

Opatz, Till .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8243-8253

[9] Electrochemical oxidation of 2-substituted piperidines as a key step towards the synthesis of hydroxylated γ-amino acids [J].

Bodmann, K ;

Bug, T ;

Steinbeisser, S ;

Kreuder, R ;

Reiser, O .

TETRAHEDRON LETTERS, 2006, 47 (13) :2061-2064

[10] 2-CYANO DELTA-3 PIPERIDINES .6. A GENERAL-METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CIS AND TRANS 2,6-DIALKYLPIPERIDINE ALKALOIDS [J].

BONIN, M ;

ROMERO, JR ;

GRIERSON, DS ;

HUSSON, HP .

TETRAHEDRON LETTERS, 1982, 23 (33) :3369-3372

← 1 2 3 4 5 6 →