AN ASYMMETRIC TOTAL SYNTHESIS OF MARTINELLIC ACID

被引：4

作者：

Badarinarayana, Vivek ^{[1
]}

Mahmud, Hossen ^{[1
]}

Lovely, Carl J. ^{[1
]}

机构：

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

HETEROCYCLES | 2017年 / 95卷 / 02期

关键词：

Alkaloid; Pyrroloquinoline; Cross-Coupling Reaction; Cycloaddition Reaction; Guanidine; FORMAL TOTAL-SYNTHESIS; (-)-MARTINELLIC ACID; (+/-)-MARTINELLIC ACID; CYCLOADDITION APPROACH; CYCLIZATION REACTIONS; CORE; LACTONES; LACTAMS; AGENTS;

D O I：

10.3987/COM-16-S(S)81

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an asymmetric total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid starting from pyrroglutamic acid. A convergent strategy involving a Pd-catalyzed aryl amination reaction of a chiral, non-racemic pyrrolidine derivative incorporates the C2-chiral center which controls the remaining two stereocenters. Elaboration of this adduct through a Grieco-elimination sets the stage for a diastereoselective intramolecular [3+2] azomethine ylide-alkene cycloaddition and the construction of the remaining two chiral centers. Elaboration of the cycloadduct and incorporation the prenyl guanidine units delivered martinellic acid after removal of the protecting groups.

引用

页码：1082 / 1105

页数：24

共 33 条

[1] Total synthesis of (-)-martinellic acid [J].

Badarinarayana, Vivek ;

Lovely, Carl J. .

TETRAHEDRON LETTERS, 2007, 48 (14) :2607-2610

[2] Palladium-catalyzed aryl-amidation.: Synthesis of non-racemic N-aryl lactams [J].

Browning, RG ;

Badarinarayana, V ;

Mahmud, H ;

Lovely, CJ .

TETRAHEDRON, 2004, 60 (02) :359-365

[3] Synthesis of chiral N-aryl pyrrolidinones via a palladium-catalyzed cross-coupling reaction [J].

Browning, RG ;

Mahmud, H ;

Badarinarayana, V ;

Lovely, CJ .

TETRAHEDRON LETTERS, 2001, 42 (41) :7155-7157

[4] A diastereodivergent strategy for the asymmetric syntheses of (-)-martinellic acid and (-)-4-epi-martinellic acid [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Lee, James A. ;

Lorkin, Thomas J. A. ;

Roberts, Paul M. ;

Thomson, James E. .

TETRAHEDRON, 2013, 69 (46) :9779-9803

[5] Asymmetric Synthesis of (-)-Martinellic Acid [J].

Davies, Stephen G. ;

Fletcher, Ai M. ;

Lee, James A. ;

Lorkin, Thomas J. A. ;

Roberts, Paul M. ;

Thomson, James E. .

ORGANIC LETTERS, 2013, 15 (08) :2050-2053

[6] ENANTIOSELECTIVE SYNTHESIS OF (5R,9R)-5-PROPYL-OCTAHYDROINDOLIZINE [(-)-GEPHYROTOXIN 167B] [J].

FLEURANT, A ;

CELERIER, JP ;

LHOMMET, G .

TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :695-696

[7] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

[8] Formal total synthesis of (±)-martinellic acid [J].

He, Y ;

Moningka, R ;

Lovely, CJ .

TETRAHEDRON LETTERS, 2005, 46 (08) :1251-1254

[9] An intramolecular cycloaddition approach to pyrrolo[3,2-c]quinolones [J].

He, Y ;

Mahmud, H ;

Wayland, BR ;

Dias, HVR ;

Lovely, CJ .

TETRAHEDRON LETTERS, 2002, 43 (07) :1171-1174

[10] Cyclization reactions of N-acryloyl-2-aminobenzaldehyde derivatives:: formal total synthesis of martinellic acid [J].

He, Yong ;

Mahmud, Hossen ;

Moningka, Remond ;

Lovely, Carl J. ;

Dias, H. V. Rasika .

TETRAHEDRON, 2006, 62 (37) :8755-8769

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