Record 7988   View: Standard Glossary  HistCite Guide
Author(s): Agarwal S; Cammerer S; Filali S; Frohner W; Knoll J; Krahl MP; Reddy KR; Knolker HJ
Title: Novel routes to pyrroles, indoles and carbazoles - Applications in natural product synthesis
Source: CURRENT ORGANIC CHEMISTRY 9 (15): 1601-1614
Date: 2005 OCT
Document Type: Journal : Review
DOI:  
Language: English
Comment:  
Address: Tech Univ Dresden, Inst Organ Chem, D-01069 Dresden, Germany.
Reprint: Knolker, HJ, Tech Univ Dresden, Inst Organ Chem, Bergstr 66, D-01069
Dresden, Germany.
E-mail: joachim.knoelker@chemie.tu-dresden.de
Author Keywords:  
KeyWords Plus: TRANSITION-METAL-COMPLEXES; TRICARBONYLIRON-DIENE COMPLEXES; PALLADIUM- CATALYZED AMINATION; INHIBITOR CARBAZOQUINOCIN-C; IRON-MEDIATED SYNTHESIS; CARBONYL-PROMOTED CYCLOCARBONYLATION; MURRAYA-EUCHRESTIFOLIA HAYATA; LIGAND-EXCHANGE REACTION; DIELS-ALDER REACTIONS; 1ST TOTAL- SYNTHESIS
Abstract: Using organometallic chemistry several novel methods for the efficient construction of pyrroles, indoles, and carbazoles have been developed. The key reactions are transition metal-mediated or -catalyzed oxidative cyclizations and cycloadditions. In the present article we summarize some recent applications of these methods to short and convergent total syntheses of naturally occurring biologically active alkaloids including fused indolizidines, yohimbanes, Amaryllidaceae alkaloids, and carbazoles.
Cited References:
AGARWAL S, 2004, ORG BIOMOL CHEM, V2, P3060
AHMAN J, 1997, TETRAHEDRON LETT, V38, P6363
AKERMARK B, 1975, J ORG CHEM, V40, P1365
AKERMARK B, 1995, TETRAHEDRON LETT, V36, P1325
AMES DE, 1984, TETRAHEDRON, V40, P1919
ANGENOT L, 1978, J PHARM BELG, V33, P284
ASHCROFT WR, 1981, TETRAHEDRON, V37, P3005
AYGUN A, 2000, SYNLETT DEC, P1757
BECCALLI EM, 1994, J CHEM SOC P1, P579
BECCALLI EM, 1998, TETRAHEDRON, V54, P11675
BERGMAN J, 1990, PURE APPL CHEM, V62, P1967
BERNOTAS RC, 1991, TETRAHEDRON LETT, V32, P161
BIRCH AJ, 1968, J CHEM SOC A, P332
BIRCH AJ, 1973, J CHEM SOC P1, P1600
BIRCH AJ, 1981, J CHEM SOC P1, P1006
BITTNER S, 1991, SYNTHESIS-STUTTG MAR, P215
BOGER DL, 2000, J ORG CHEM, V65, P9120
BOUAZIZ Z, 2000, HETEROCYCLES, V52, P977
CARDELLINA JH, 1979, TETRAHEDRON LETT, P4915
CERUTTI PA, 1985, SCIENCE, V227, P375
CHAKRABORTY DP, 1991, PROGR CHEM ORGANIC N, V57, P71
CHAKRABORTY DP, 1993, ALKALOIDS, V44, P257
CHAKRABORTY DP, 2003, PROGR CHEM ORGANIC N, V85, P125
CHATTOPADHYAY S, 1983, PLANTA MED, V49, P252
CHOSHI T, 1996, TETRAHEDRON LETT, V37, P2953
CHOSHI T, 1997, J ORG CHEM, V62, P2535
CLEMO GR, 1946, J CHEM SOC, P617
CLEMO GR, 1949, J CHEM SOC, P48
CORSANO S, 1960, ANN CHIM, V50, P75
DANHEISER RL, 1990, J AM CHEM SOC, V112, P3093
DEWICK PM, 2002, MED NATURAL PRODUCTS
DUVAL E, 2004, TETRAHEDRON LETT, V45, P5411
FERREIRA VF, 2001, ORG PREP PROCED INT, V33, P411
FISCHER EO, 1960, ANGEW CHEM, V72, P919
FREDERICH M, 2002, J NAT PROD, V65, P1381
FROHNER W, 2004, HETEROCYCLES, V63, P2393
FURSTNER A, 2003, ANGEW CHEM INT EDIT, V42, P3528
FURSTNER A, 2003, ANGEW CHEM, V115, P3706
FURUKAWA H, 1985, CHEM PHARM BULL, V33, P1320
FURUKAWA H, 1985, CHEM PHARM BULL, V33, P4132
FURUKAWA H, 1986, CHEM PHARM BULL, V34, P2672
FURUKAWA H, 1993, TRENDS HETEROCYCL CH, V3, P185
FURUKAWA H, 1994, J INDIAN CHEM SOC, V71, P303
GHOSAL S, 1981, PHYTOCHEMISTRY, V20, P2003
GRIBBLE GW, 1996, COMPREHENSIVE HETERO, V2, P207
HAGIWARA H, 2000, TETRAHEDRON, V56, P5807
HAGIWARA H, 2001, CHEM PHARM BULL, V49, P881
HAIGWARA H, 1998, CHEM PHARM BULL, V46, P1948
HALL RJ, 1992, J CHEM SOC P1, P3439
HALLIWELL B, 1990, METHOD ENZYMOL, V186, P1
HAMMOND B, 1985, CAN J PHYSIOL PHARM, V63, P173
HARAYAMA T, 2004, TETRAHEDRON, V60, P1611
HARROWVEN DC, 1999, SYNTHESIS-STUTTG AUG, P1300
HARTWIG JF, 1998, ANGEW CHEM INT EDIT, V37, P2046
HARTWIG JF, 1998, ANGEW CHEM, V110, P2154
HENRY PM, 2002, HDB ORGANOPALLADIUM, V2
HESSE M, 2002, ALKALOIDS NATURES CU
HIBINO S, 1995, ADV NITROG HETERCYC, V1, P205
HOOK DJ, 1990, J ANTIBIOT, V43, P1347
IMBRIGLIO JE, 2001, TETRAHEDRON LETT, V42, P6957
ITO C, 1990, CHEM PHARM BULL, V38, P1548
ITOH T, 2002, HETEROCYCLES, V58, P115
ITOH T, 2004, HETEROCYCLES, V63, P655
KALIVRETENOS A, 1991, J ORG CHEM, V56, P2883
KAM TS, 1998, PHYTOCHEMISTRY, V47, P145
KANEDA M, 1981, HETEROCYCLES, V15, P993
KANEDA M, 1988, J ANTIBIOT, V41, P602
KANO S, 1980, J CHEM SOC CHEM COMM, P1241
KANO S, 1981, J ORG CHEM, V46, P3856
KAWASAKI T, 1989, J CHEM SOC CHEM COMM, P43
KAWASAKI T, 1993, J CHEM SOC P1, P1777
KAWASAKI T, 1994, J INDIAN CHEM SOC, V71, P443
KNOLKER HJ, 1991, ORGANIC SYNTHESIS VI, P119
KNOLKER HJ, 1992, SYNLETT MAY, P371
KNOLKER HJ, 1992, SYNLETT, P1002
KNOLKER HJ, 1993, SYNLETT, P924
KNOLKER HJ, 1993, TETRAHEDRON, V49, P841
KNOLKER HJ, 1994, J PRAK CHEM-CHEM ZTG, V336, P277
KNOLKER HJ, 1994, SYNLETT, P194
KNOLKER HJ, 1994, TETRAHEDRON LETT, V35, P1695
KNOLKER HJ, 1994, TETRAHEDRON, V50, P10893
KNOLKER HJ, 1995, ADV NITROGEN HETEROC, V1, P173
KNOLKER HJ, 1995, TETRAHEDRON LETT, V36, P5339
KNOLKER HJ, 1995, TETRAHEDRON LETT, V36, P7647
KNOLKER HJ, 1996, J PRAK CHEM-CHEM ZTG, V338, P190
KNOLKER HJ, 1996, TETRAHEDRON LETT, V37, P9183
KNOLKER HJ, 1997, TETRAHEDRON LETT, V38, P1535
KNOLKER HJ, 1997, TETRAHEDRON LETT, V38, P4051
KNOLKER HJ, 1998, J CHEM SOC PERK 0121, P173
KNOLKER HJ, 1998, ORGANOMETALLICS, V17, P3916
KNOLKER HJ, 1998, TETRAHEDRON LETT, V39, P8267
KNOLKER HJ, 1998, TRANSITION METALS OR, V1, P534
KNOLKER HJ, 1999, ANGEW CHEM INT EDIT, V38, P2064
KNOLKER HJ, 1999, ANGEW CHEM INT EDIT, V38, P702
KNOLKER HJ, 1999, ANGEW CHEM, V111, P2196
KNOLKER HJ, 1999, ANGEW CHEM, V111, P727
KNOLKER HJ, 1999, CHEM SOC REV, V28, P151
KNOLKER HJ, 1999, J PRAKT CHME, V40, P8078
KNOLKER HJ, 1999, SYNLETT MAY, P596
KNOLKER HJ, 1999, TETRAHEDRON LETT, V40, P8078
KNOLKER HJ, 1999, TETRAHEDRON, V55, P10391
KNOLKER HJ, 2000, CHEM REV, V100, P2941
KNOLKER HJ, 2000, SYNTHESIS-STUTTG DEC, P2131
KNOLKER HJ, 2000, TETRAHEDRON LETT, V41, P5035
KNOLKER HJ, 2000, TETRAHEDRON, V56, P2259
KNOLKER HJ, 2001, PURE APPL CHEM, V73, P1075
KNOLKER HJ, 2002, CHEM REV, V102, P4303
KNOLKER HJ, 2002, SYNTHESIS-STUTTG MAR, P557
KNOLKER HJ, 2003, CHEM COMMUN, P1170
KNOLKER HJ, 2003, EUR J ORG CHEM FEB, P740
KNOLKER HJ, 2003, HETEROCYCLES, V60, P1049
KNOLKER HJ, 2003, SYNLETT 0902, P1752
KNOLKER HJ, 2004, CURR ORG SYNTH, V1, P309
KNOLKER HJ, 2004, SYNLETT 0218, P528
KNOLKER HJ, 2004, SYNLETT 0809, P1767
KNOLKER HJ, 2004, SYNLETT, P705
KNOLKER HJ, 2004, TRANSITION METALS OR, V1, P585
KNOLKER HJ, 2005, TETRAHEDRON LETT, V46, P1173
KNOLKER HJ, 2005, TOP CURR CHEM, V244, P115
KOTADA N, 1997, J ANTIBIOT, V50, P770
LEDNICER D, 1998, STRATEGIES ORGANIC D
LI JJ, 2000, PALLADIUM HETEROCYCL
LOUIE J, 1997, J ORG CHEM, V62, P1268
MANDAL SB, 1988, J ORG CHEM, V53, P4236
MASSIOT G, 1987, PHYTOCHEMISTRY, V26, P2839
MCKEAN DR, 1987, J ORG CHEM, V52, P422
MERLINI L, 1967, TETRAHEDRON, V23, P3129
MEYERS AI, 1984, TETRAHEDRON LETT, V25, P2641
MIKI Y, 1999, TETRAHEDRON LETT, V40, P4347
MILLER RB, 1980, TETRAHEDRON LETT, V21, P3319
MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803
MOODY CJ, 1989, J CHEM SOC P1, P376
MOODY CJ, 1994, SYNLETT, P681
MUCI AR, 2002, TOP CURR CHEM, V219, P131
NEGISHI EI, 1985, J AM CHEM SOC, V107, P6639
NEGISHI KE, 1979, SYNTHESIS-STUTTGART, P501
OAME I, 1998, APPL ORGANOMETALLIC
OGLIARUSO MA, 1965, CHEM REV, V65, P261
ORITO K, 1988, HETEROCYCLES, V27, P2403
PADWA A, 1999, J ORG CHEM, V64, P3595
PEARSON AJ, 1981, J CHEM SOC P1, P1614
PEARSON AJ, 1982, J CHEM SOC P1, P2641
PEARSON AJ, 1986, ORGANOMETALLICS, V5, P2075
PEARSON AJ, 1991, J CHEM SOC CHEM COMM, P202
PEARSON AJ, 1992, ORGANOMETALLICS, V11, P4096
PEARSON AJ, 1994, ORGANOMETALLICS, V13, P578
PEARSON AJ, 1997, SYNLETT NOV, P1281
PEARSON AJ, 2002, ORG LETT, V4, P2837
PEUBELOCOU N, 1973, PHYTOCHEMISTRY, V12, P199
PINDUR U, 1990, CHIMIA, V44, P406
PINDUR U, 1995, ADV NITROG HETERCYC, V1, P121
RAINIER JD, 2000, J ORG CHEM, V65, P7272
RAMESH K, 1987, J NAT PROD, V50, P932
RAND CL, 1981, J ORG CHEM, V46, P4097
SAHA C, 1998, PHYTOCHEMISTRY, V48, P363
SAKANO K, 1980, J ANTIBIOT, V33, P683
SAKANO K, 1980, J ANTIBIOT, V33, P961
SCHELL FM, 1983, TETRAHEDRON LETT, V24, P1883
SCHITTLER E, 1948, HELV CHIM ACTA, V31, P128
SHIN K, 1996, SYNLETT SEP, P922
SHOV Y, 1974, J CHEM SOC CHEM COMM, P336
SOOS T, 1999, TETRAHEDRON LETT, V40, P8607
STARK LM, 2000, J ORG CHEM, V65, P3227
STILLE JK, 1986, ANGEW CHEM INT EDIT, V25, P508
SUNDBERG RJ, 1996, COMPREHENSIVE HETE 2, V2, P119
SWAN GA, 1949, J CHEM SOC, P1720
TAKACS JM, 2003, CURR ORG CHEM, V7, P369
TAKANO S, 1981, HETEROCYCLES, V16, P1479
TAKEYA K, 1989, EUR J PHARMACOL, V169, P137
TANAKA M, 1995, J ANTIBIOT, V48, P326
TASLER S, 2002, CHEM REC, V2, P114
TORRES JC, 2004, TETRAHEDRON, V60, P9889
TSUJI J, 1995, PALLADIUM REAGENTS C, PCH3
VANHORN DE, 1978, J AM CHEM SOC, V100, P2252
WEINSTEIN B, 1976, J ORG CHEM, V41, P875
WINTERFELDT E, 1975, SYNTHESIS-STUTTGART, P617
WITULSKI B, 2002, ANGEW CHEM INT EDIT, V41, P3281
WITULSKI B, 2002, ANGEW CHEM, V114, P3415
WOLFE JP, 1997, J ORG CHEM, V62, P1264
WOLKENBERG SE, 2002, J ORG CHEM, V67, P7361
WU TS, 1997, HETEROCYCLES, V45, P969
YAMASAKI K, 1983, J ANTIBIOT, V36, P552
YASUHARA A, 2002, CHEM PHARM BULL, V50, P143
YOGO M, 1991, CHEM PHARM BULL, V39, P328
ZHANG QY, 2002, TETRAHEDRON, V58, P6795