Palladium-promoted cascade reactions of isonitriles and 6-iodo-N-propargylpyridones:: Synthesis of mappicines, camptothecins, and homocamptothecins

被引：99

作者：

Curran, DP ^{[1
]}

Du, W ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 19期

关键词：

D O I：

10.1021/ol026408d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ambient-temperature reactions of electron-rich aryl isonitriles with substituted 6-iodo-N-propargylpyridones in the presence of silver carbonate and palladium acetate produce 11H-indolizino[1,2b]quinolin-9-ones in good to excellent yield. Experimental evidence suggests that the process coccurs though organopalladium rather than radical intermediates. It is applied to synthesis analogues of mappicine and camptothecin, including the silatecans DB-67 and DB-91 (homo-DB-67).

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页码：3215 / 3218

页数：4

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共 41 条

[31] FACILE SYNTHESIS OF VICINAL DICARBONYL AND TRICARBONYL COMPOUNDS BY SMI2-MEDIATED DOUBLE INSERTION OF ISOCYANIDES INTO ORGANIC HALIDES [J].

MURAKAMI, M ;

MASUDA, H ;

KAWANO, T ;

NAKAMURA, H ;

ITO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :1-2

[32] [2-(BENZYLOXY)-1-(N-2,6-XYLYLIMINO)ETHYL]SAMARIUM AS A SYNTHETIC EQUIVALENT TO ALPHA-HYDROXYACETYL ANION [J].

MURAKAMI, M ;

KAWANO, T ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2437-2439

[33] PALLADIUM-CATALYZED REACTION OF 5-METHYLENE-1,3-DIOXOLAN-2-ONES - A NEW ACCESS TO AND REACTIVITY OF OXATRIMETHYLENEMETHANE PALLADIUM [J].

OHE, K ;

MATSUDA, H ;

ISHIHARA, T ;

OGOSHI, S ;

CHATANI, N ;

MURAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1173-1177

[34] SIGMA-ALKYL OR SIGMA-ACYL ISOCYANIDE COMPLEXES OF NICKEL(II) AND PALLADIUM(II) . PREPARATION AND SUCCESSIVE INSERTION REACTIONS [J].

OTSUKA, S ;

NAKAMURA, A ;

YOSHIDA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (25) :7196-&

[35] SYNTHESIS AND ANTI-HSV ACTIVITY OF METHYLENEDIOXY MAPPICINE KETONE ANALOGS [J].

PENDRAK, I ;

WITTROCK, R ;

KINGSBURY, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2912-2915

[36] CONSTITUENTS OF NOTHAPODYTES-FOETIDA [J].

PIRILLO, A ;

VEROTTA, L ;

GARIBOLDI, P ;

TORREGIANI, E ;

BOMBARDELLI, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (05) :583-587

[37] Cascade radical reactions catalyzed by a Pd/light system: Cyclizative multiple carbonylation of 4-alkenyl iodides [J].

Ryu, I ;

Kreimerman, S ;

Araki, F ;

Nishitani, S ;

Oderaotoshi, Y ;

Minakata, S ;

Komatsu, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3812-3813

[38] Tandem radical reactions of carbon monoxide, isonitriles, and other reagent equivalents of the geminal radical acceptor radical precursor synthon [J].

Ryu, I ;

Sonoda, N ;

Curran, DP .

CHEMICAL REVIEWS, 1996, 96 (01) :177-194

[39]

Studer A, 2002, SYNTHESIS-STUTTGART, P835

[40] NICKEL(0)-PROMOTED CYCLIZATION OF ENYNES WITH ISOCYANIDES - A NEW ROUTE TO POLYCYCLIC CYCLOPENTENONE SKELETONS [J].

TAMAO, K ;

KOBAYASHI, K ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1286-1288

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