Enantioselective synthesis of 2-[(3-ethyl-4-piperidyl)methyl]indoles from a phenylglycinol-derived lactam:: formal synthesis of Strychnos alkaloids

被引：9

作者：

Amat, Mercedes ^{[1
]}

Llor, Nuria ^{[1
]}

Checa, Begona ^{[1
]}

Perez, Maria ^{[1
]}

Bosch, Joan ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 38期

关键词：

phenylglycinol; Strychnos alkaloids; piperidines; indoles; oxazolopiperidone lactams;

D O I：

10.1016/j.tetlet.2007.07.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereodivergent synthesis of enantiopure cis- and traiis-2-[(3-ethyl-4-piperidyl)methyl]indole (cis-1b and trans-1b) from a common phenylglycino]-derived oxazolopiperidone lactam 3 is reported. The key step is a stereocontrolled conjugate addition, either under kinetic or thermodynamic control, of the dilithium salt of 2-(2-indolyl)-1,3-dithiane to unsaturated lactam 3. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6722 / 6725

页数：4

共 35 条

[21] General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids
Deiters, Alexander
Pettersson, Martin
Martin, Stephen F.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) : 6547 - 6561
[22] Deslongchamps P., 1983, Stereoelectronic Effects in Organic Chemistry
[23] Chiral oxazolopiperidone lactams: Versatile intermediates for the enantioselective synthesis of piperidine-containing natural products
Escolano, Carmen
Amat, Mercedes
Bosch, Joan
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (32) : 8199 - 8207
[24] Synthetic applications of 2-(1,3-dithian-2-yl)indoles .6. Synthesis of 20-epidasycarpidone
Forns, P
Diez, A
Rubiralta, M
Solans, X
FontBardia, M
[J]. TETRAHEDRON, 1996, 52 (10) : 3563 - 3574
[25] Conjugate additions of sulfur-stabilized anions to unsaturated lactams.: Synthesis of polyfunctionalized benzo[a]quinolizinone systems
Garcia, Eva
Lete, Esther
Sotomayor, Nuria
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) : 6776 - 6784
[26] TOTAL SYNTHESIS OF ULEINE-TYPE AND STRYCKNOS ALKALOIDS THROUGH A COMMON INTERMEDIATE
GRACIA, J
CASAMITJANA, N
BONJOCH, J
BOSCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) : 3939 - 3951
[27] Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions
Groaning, MD
Meyers, AI
[J]. TETRAHEDRON, 2000, 56 (51) : 9843 - 9873
[28] JOULE JA, 1983, INDOLES MONOTERPEN 4, V25, pCH6
[29] Chiral bicyclic lactams: Useful precursors and templates for asymmetric syntheses
Meyers, AI
Brengel, GP
[J]. CHEMICAL COMMUNICATIONS, 1997, (01) : 1 - 8
[30] PERLMUTTER P, 1992, CONJUGATE ADDITION R, P25

← 1 2 3 4 →