Diastereoselective Syntheses of Indoloquinolizidines by a Pictet-Spengler/Lactamization Cascade

被引：63

作者：

Fang, Huihui ^{[1
]}

Wu, Xiaoyu ^{[1
]}

Nie, Linlin ^{[1
]}

Dai, Xiaoyang ^{[1
]}

Chen, Jie ^{[1
]}

Cao, Weiguo ^{[1
]}

Zhao, Gang ^{[2
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Organ Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 23期

基金：

美国国家科学基金会;

关键词：

SPENGLER REACTION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALKALOID SYNTHESIS; INDOLE ALKALOIDS; DERIVATIVES; CIS; (+)-GEISSOSCHIZINE; EPIMERIZATION;

D O I：

10.1021/ol101922h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient diastereoselective synthesis of highly functionalized indolo[2,3-alpha]quinolizidines adopting a cis H2/H12b geometry has been realized by a Pictet-Spengler/lactamization cascade sequence. The absolute stereochemistry at C2, C3, and C12b was governed by the originally created chirality of the Michael adduct through organocatalyzed conjugate addition of dialkyl malonates to alpha,beta-unsaturated aldehydes.

引用

页码：5366 / 5369

页数：4

共 52 条

[1] A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis [J].

Allin, SM ;

Thomas, CI ;

Allard, JE ;

Doyle, K ;

Elsegood, MRJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4179-4186

[2] An asymmetric synthesis of both enantiomers of the indole alkaloid deplancheine [J].

Allin, SM ;

Thomas, CI ;

Doyle, K ;

Elsegood, MRJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :357-359

[3] Stereoselective synthesis of isoquinoline derivatives from bicyclic lactam templates [J].

Allin, SM ;

Vaidya, DG ;

James, SL ;

Allard, JE ;

Smith, TAD ;

McKee, V ;

Martin, WP .

TETRAHEDRON LETTERS, 2002, 43 (20) :3661-3663

[4] Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets [J].

Allin, Steven M. ;

Duffy, Liam J. ;

Bulman Page, Philip C. ;

McKee, Vickie ;

Edgar, Mark ;

McKenzie, Michael J. ;

Amat, Mercedes ;

Bassas, Oriol ;

Santos, Maria M. M. ;

Bosch, Joan .

TETRAHEDRON LETTERS, 2006, 47 (32) :5713-5716

[5] An enantioselective entry to cis-perhydroisoquinolines [J].

Amat, M ;

Pérez, M ;

Minaglia, AT ;

Casamitjana, N ;

Bosch, J .

ORGANIC LETTERS, 2005, 7 (17) :3653-3656

[6] Enantioselective spirocyclizations from tryptophanol-derived oxazolopiperidone lactams [J].

Amat, Mercedes ;

Santos, Maria M. M. ;

Gomez, Antonia M. ;

Jokic, Danica ;

Molins, Elies ;

Bosch, Joan .

ORGANIC LETTERS, 2007, 9 (15) :2907-2910

[7] Straightforward methodology for the enantioselective synthesis of benzo[a]- and indolo[2,3-a]quinolizidines [J].

Amat, Mercedes ;

Santos, Maria M. M. ;

Bassas, Oriol ;

Llor, Nuria ;

Escolano, Carmen ;

Gomez-Esque, Arantxa ;

Molins, Elies ;

Allin, Steven M. ;

McKee, Vickie ;

Bosch, Joan .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5193-5201

[8]

[Anonymous], 2007, Chem. Rev

[9]

[Anonymous], 2004, Acc. Chem. Res

[10]

Baxter E.W., 1992, Alkaloids: Chemical and Biological Perspectives, V8, P197

← 1 2 3 4 5 6 →