Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines

被引：54

作者：

Bélanger, G ^{[1
]}

Hong, FT ^{[1
]}

Overman, LE ^{[1
]}

Rogers, BN ^{[1
]}

Tellew, JE ^{[1
]}

Trenkle, WC ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 22期

关键词：

D O I：

10.1021/jo026282y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The construction of triazacyclopenta[cd]pentalene diesters 6 by the reaction of dihydropyrrole alpha-ketoesters 3 with acylated hydrazines was evaluated further as a potential central strategic step in the total syntheses of complex guanidine alkaloids such as palau' amine and styloguanidine. Successful cyclocondensations were realized with acid-stable 2,2,2-trichloroethyl carbazate and thiosemicarbazide, but not tert-butyl carbazate. The substituent on the pyrrolidine nitrogen can be alkoxycarbonyl, sulfonyl, or an N-alkyl-2-acylpyrrole group. Siloxy substitution at C1 of the alpha-ketoester side chain is also tolerated.

引用

收藏

页码：7880 / 7883

页数：4

相关论文

共 22 条

[1] Ring-enlarging cyclohexane annulations [J].

Ando, S ;

Minor, KP ;

Overman, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6379-6387

[2] 3-PYRROLIDINONES BY INTRAMOLECULAR CONDENSATION [J].

BLAKE, J ;

RAPOPORT, H ;

WILLSON, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) :5293-&

[3] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[4] A CONVENIENT METHOD FOR THE SYNTHESIS OF ALPHA-KETOESTERS FROM ALDEHYDES [J].

HORNE, D ;

GAUDINO, J ;

THOMPSON, WJ .

TETRAHEDRON LETTERS, 1984, 25 (33) :3529-3532

[5] A MILD PROCEDURE FOR THE GENERATION OF AZOMETHINE IMINES - STEREOCHEMICAL FACTORS IN THE INTRAMOLECULAR 1,3-DIPOLAR ADDITION OF AZOMETHINE IMINES AND A SYNTHETIC APPROACH TO SAXITOXIN [J].

JACOBI, PA ;

BROWNSTEIN, A ;

MARTINELLI, M ;

GROZINGER, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (01) :239-241

[6] TOTAL SYNTHESIS OF (+/-)-SAXITOXIN [J].

JACOBI, PA ;

MARTINELLI, MJ ;

POLANC, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5594-5598

[7] TRIETHYLAMINE-MEDIATED GENERATION OF A SYNTHETIC EQUIVALENT OF PARENT AZOMETHINE IMINE BY CONDENSATION OF ETHYL 3-BENZYLCARBAZATE WITH PARAFORMALDEHYDE [J].

KANEMASA, SJ ;

TOMOSHIGE, N ;

WADA, EJ ;

TSUGE, O .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (12) :3944-3949

[8]

MARTINELLI MJ, 1986, CROAT CHEM ACTA, V59, P267

[9] NEW ACYL ANION EQUIVALENT - A SHORT ROUTE TO THE ENOL LACTAM INTERMEDIATE IN CYTOCHALASIN SYNTHESIS [J].

NAKAMURA, E .

TETRAHEDRON LETTERS, 1981, 22 (07) :663-666

[10]

OPPOLZER W, 1977, ANGEW CHEM INT EDIT, V16, P10, DOI 10.1002/anie.197700101