Total Synthesis of the Bridged Indole Alkaloid Apparicine

被引：58

作者：

Bennasar, M. -Lluisa ^{[1
]}

Zulaica, Ester

Sole, Daniel

Roca, Tomas

Garcia-Diaz, Davinia

Alonso, Sandra

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

关键词：

RING-CLOSING METATHESIS; STEREOCONTROLLED SYNTHESIS; OLEFIN ISOMERIZATION; CONCISE SYNTHESIS; STRYCHNOS; CONSTRUCTION; ASPIDOSPERMA; CYCLOPROPANATION; AZEPINOINDOLE; BIOSYNTHESIS;

D O I：

10.1021/jo901986v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An indole-templated ring-closing metathesis or it 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.

引用

页码：8359 / 8368

页数：10

共 64 条

[1] FRAGMENTATION OF NN-DIMETHYLTRYPTAMINE OXIDE AND RELATED COMPOUNDS - A POSSIBLE IMPLICATION IN INDOLE ALKALOID BIOSYNTHESIS [J].

AHOND, A ;

CAVE, A ;

KANFAN, C ;

LANGLOIS, Y ;

POTIER, P .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (09) :517-&

[2]

AKHTER L, 1978, TETRAHEDRON LETT, P4137, DOI 10.1016/S0040-4039(01)95164-0

[3] Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo .

CHEMICAL REVIEWS, 2009, 109 (08) :3817-3858

[4]

ALVAREZ M, 2001, ALKALOIDS, V57, pCH4

[5]

ATTA-UR-RAHMAN, 1985, Heterocycles (Tokyo), V23, P2975

[6]

ATTAURRAHMAN, 1987, PLANTA MED, P57, DOI 10.1055/s-2006-962620

[7] ISOLATION OF 19,20-Z-VALLESAMINE AND 19,20-E-VALLESAMINE FROM ALSTONIA-SCHOLARIS [J].

ATTAURRAHMAN ;

ALVI, KA ;

ABBAS, SA ;

VOELTER, W .

HETEROCYCLES, 1987, 26 (02) :413-419

[8]

BATTY D, 1990, SYNTHESIS-STUTTGART, P273

[9] Rapid synthesis of the ervitsine alkaloid skeleton by a sequential RCM-Heck cyclization approach [J].

Bennasar, M. -Lluisa ;

Zulaica, Ester ;

Sole, Daniel ;

Alonso, Sandra .

SYNLETT, 2008, (05) :667-670

[10] Novel 7- and 8-endo 2-indolylacyl radical cyclizations:: Efficient construction of azepino- and azocinoindoles [J].

Bennasar, M.-Lluisa ;

Roca, Tomas ;

Garcia-Diaz, Davinia .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4562-4565

← 1 2 3 4 5 6 7 →