[2+2+2] Cycloadditions of Alkynylynamides - A Total Synthesis of Perlolyrine and the First Total Synthesis of "Isoperlolyrine"

被引：57

作者：

Dassonneville, Benjamin ^{[1
]}

Witulski, Bernhard ^{[2
]}

Detert, Heiner ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany

[2] ENSICAEN, Lab Chim Mol & Thioorgan, UMR 6507, F-14050 Caen, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 15期

关键词：

Heterocycles; Alkaloids; Cycloaddition; Rhodium; Ruthenium; BETA-CARBOLINE ALKALOIDS; ONE-STEP SYNTHESIS; CATALYZED CYCLOADDITION; FLEXIBLE SYNTHESIS; GAMMA-CARBOLINE; 1,6-DIYNES; NITRILES; ALKYNES; CONSTRUCTION; PYRIDINES;

D O I：

10.1002/ejoc.201100121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total syntheses of the carboline alkaloids perlolyrine and "isoperlolyrine" are reported. Key-steps of the syntheses are Negishi coupling reactions on alkynylynamides and their metal-catalyzed [2+2+2] cycloadditions with nitriles to form the beta- and gamma-carboline cores. The choice of the catalyst strongly affects the beta/gamma ratio. Spectroscopic features of the gamma-isomer are distinctly different from those of the naturally occurring isoperlolyrine.

引用

页码：2836 / 2844

页数：9

共 90 条

[81] Alkaloids and other constituents from Tribulus terrestris [J].

Wu, TS ;

Shi, LS ;

Kuo, SC .

PHYTOCHEMISTRY, 1999, 50 (08) :1411-1415

[82] Synthesis of 2-haloalkylpyridines via Cp*RuCl-catalyzed cycloaddition of 1,6-diynes with α-halonitriles.: Unusual halide effect in catalytic cyclocotrimerization [J].

Yamamoto, Y ;

Kinpara, K ;

Nishiyama, H ;

Itoh, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (15) :1913-1916

[83] Cp*RuCl-catalyzed [2+2+2] cycloadditions of α,ω-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles [J].

Yamamoto, Y ;

Kinpara, K ;

Saigoku, F ;

Takagishi, H ;

Okuda, S ;

Nishiyama, H ;

Itoh, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) :605-613

[84] Significant chemo- and regioselectivies in the Ru(II)-catalyzed [2+2+2] cycloaddition of 1,6-diynes with dicyanides [J].

Yamamoto, Y ;

Ogawa, R ;

Itoh, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :6189-6190

[85] Ruthenium(II)-catalyzed [2+2+2] cycloaddition of 1,6-diynes with electron-deficient nitriles [J].

Yamamoto, Y ;

Okuda, S ;

Itoh, K .

CHEMICAL COMMUNICATIONS, 2001, (12) :1102-1103

[86] Ruthenium-catalyzed cycloaddition of 1,6-diynes and nitriles under mild conditions: Role of the coordinating group of nitriles [J].

Yamamoto, Yoshihiko ;

Kinpara, Keisuke ;

Ogawa, Ryuji ;

Nishiyama, Hisao ;

Itoh, Kenji .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5618-5631

[87] Synthesis and biological evaluation of analogues of cryptolepine, an alkaloid isolated from the Suriname rainforest [J].

Yang, SW ;

Abdel-Kader, M ;

Malone, S ;

Werkhoven, MCM ;

Wisse, JH ;

Bursuker, I ;

Neddermann, K ;

Fairchild, C ;

Raventos-Suarez, C ;

Menendez, AT ;

Lane, K ;

Kingston, DGI .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (07) :976-983

[88] EFFECTS OF ANTHRAQUINONES OF POLYGONUM-CUSPIDATUM ON HL-60 CELLS [J].

YEH, SF ;

CHOU, TC ;

LIU, TS .

PLANTA MEDICA, 1988, (05) :413-414

[89] Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes [J].

Zhang, HM ;

Larock, RC .

TETRAHEDRON LETTERS, 2002, 43 (08) :1359-1362

[90] Synthesis of annulated γ-carbolines by palladium-catalyzed intramolecular iminoannulation [J].

Zhang, HM ;

Larock, RC .

ORGANIC LETTERS, 2002, 4 (18) :3035-3038

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