Abstract
This review article gives a detailed account on the chemistryof the pyrrole-imidazole alkaloids from marine sponges. The pyrrole-imidazolealkaloids share a key building block, oroidin being the underlyingstructural motif of a diverse range of exclusively marine alkaloids.After outlining the reactivity of 2-amino-4(5)-vinylimidazoles,biomimetic and non-biomimetic total syntheses of the non-cyclized,cyclized, and ‘dimerized’ pyrrole-imidazole alkaloidsdeveloped over the past 30 years are discussed in a comprehensivemanner. Beyond the identified pyrrole-imidazole alkaloids the theoreticalcyclization map based on oroidin contains many white spots and therebyopportunities to assemble novel pyrrole-imidazole alkaloids notobserved in nature before.
1 Introduction
1.1 Alkaloid Economy
1.2 Biosynthesis
1.3 Biological Activity
2 Reactivity of Partial Structures
2.1 2-Aminoimidazole
2.2 Pyrrole-2-carboxamide
3 Non-Cyclized Pyrrole-Imidazole Alkaloids
3.1 Starting from Imidazole
3.2 Assembly of the Imidazole Portion
4 Biomimetic Syntheses
4.1 Cyclized Monomers
4.2 Dimeric Pyrrole-Imidazole Alkaloids
5 Non-Biomimetic Approaches
5.1 Completed Syntheses
5.2 Under Construction
6 Cyclization Map
7 Conclusion
Key words
alkaloids - diversity - imidazole - marinenatural products - pyrrole
References
1 Franck B.
Angew.Chem., Int. Ed. Engl.
1979,
18:
429 ; Angew. Chem. 1979 , 91 , 453
2 Al Mourabit A.
Potier P.
Eur. J. Org. Chem.
2001,
237
3a Forenza S.
Minale L.
Riccio R.
Fattorusso E.
J. Chem.Soc., Chem. Commun.
1971,
1129
3b Garcia EE.
Benjamin LE.
Fryer RI.
J. Chem. Soc., Chem. Commun.
1973,
78
3c Cimino G.
DeStefano S.
Minale L.
Sodano G.
Comp. Biochem. Physiol., Sect.B
1975,
50:
279
3d Nakamura H.
Ohizumi Y.
Kobayashi J.
Hirata Y.
Tetrahedron Lett.
1984,
25:
2475
3e Kobayashi J.
Ohizumi Y.
Nakamura H.
Hirata Y.
Experientia
1986,
42:
1176
3f Morales JJ.
Rodríguez AD.
J.Nat. Prod.
1991,
54:
629
3g Assmann M.
Zea S.
Köck M.
J.Nat. Prod.
2001,
64:
1593
4a Chevolot L.
Padua S.
Ravi BN.
Blyth PC.
Scheuer PJ.
Heterocycles
1977,
7:
891
4b Fathi-Afshar R.
Allen TM.
Can. J. Chem.
1988,
66:
45
4c Cafieri F.
Fattorusso E.
Mangoni A.
Taglialatela-Scafati O.
Tetrahedron Lett.
1996,
37:
3587
4d Cafieri F.
Carnuccio R.
Fattorusso E.
Taglialatela-Scafati O.
Vallefuoco T.
Bioorg.Med. Chem. Lett.
1997,
7:
2283
4e Uemoto H.
Tsuda M.
Kobayashi J.
J.Nat. Prod.
1999,
62:
1581
5 Tsuda M.
Uemoto H.
Kobayashi J.
TetrahedronLett.
1999,
40:
5709
6a Jiménez C.
Crews P.
TetrahedronLett.
1994,
35:
1375
6b Kobayashi J.
Inaba K.
Tsuda M.
Tetrahedron
1997,
53:
16679
7a Sharma GM.
Burkholder PR.
J. Chem. Soc., Chem. Commun.
1971,
151
7b Pettit GR.
McNulty J.
Herald DL.
Doubek DL.
Chapuis J.-C.
Schmidt JM.
Tackett LP.
Boyd MR.
J. Nat. Prod.
1997,
60:
180
8 Fattorusso E.
Taglialatela-Scafati O.
Tetrahedron Lett.
2000,
41:
9917
9a Sharma GM.
Buyer JS.
Pomerantz MW.
J.Chem. Soc., Chem. Commun.
1980,
435
9b Mattia CA.
Mazzarella L.
Puliti R.
Acta Crystallogr., Sect. B
1982,
38:
2513
9c Cimino G.
De Rosa S.
De Stefano S.
Mazzarella L.
Puliti R.
Sodano G.
Tetrahedron Lett.
1982,
23:
767
9d Kitagawa I.
Kobayashi M.
Kitanaka K.
Kido M.
Kyogoku Y.
Chem.Pharm. Bull.
1983,
31:
2321
9e Schmitz FJ.
Gunasekera SP.
Lakshmi V.
Tillekeratne LMV.
J.Nat. Prod.
1985,
48:
47
9f Albizati KF.
Faulkner DJ.
J.Org. Chem.
1985,
50:
4163
9g Kobayashi J.
Ohizumi Y.
Nakamura H.
Hirata Y.
Wakamatsu K.
Miyazawa T.
Experientia
1986,
42:
1064
9h Pettit GR.
Herald CL.
Leet JE.
Gupta R.
Schaufelberger DE.
Bates RB.
Clewlow PJ.
Doubek DL.
Manfredi KP.
Can.J. Chem.
1990,
68:
1621
9i Supriyono A.
Schwarz B.
Wray V.
Witte L.
Mueller WEG.
van Soest R.
Sumaryono W.
Proksch P.
Z. Naturforsch. C: Biosci.
1995,
50:
669
9j Inaba K.
Sato H.
Tsuda M.
Kobayashi J.
J. Nat. Prod.
1998,
61:
693
9k Eder C.
Proksch P.
Wray V.
Steube K.
Bringmann G.
VanSoest RWM.
.
Ferdinandus E.
Pattisina LA.
Wiryowidagdo S.
Moka W.
J.Nat. Prod.
1999,
62:
184
10a D’Ambrosio M.
Guerriero A.
Debitus C.
Ribes O.
Pusset J.
Leroy S.
Pietra F.
J. Chem. Soc., Chem. Commun.
1993,
1305
10b D’Ambrosio M.
Guerriero A.
Chiasera G.
Pietra F.
Helv. Chim.Acta
1994,
77:
1895
10c Hong TW.
Jimenez DR.
Molinski TF.
J. Nat. Prod.
1998,
61:
158
11 Fedoreyev SA.
Il’yin SG.
Utkina NK.
Maximov OB.
Reshetnyak MV.
Antipin MuY.
Struchkov YuT.
Tetrahedron
1989,
45:
3487
12 De Nanteuil G.
Ahond A.
Guilhem J.
Poupat C.
Dau ETH.
Potier P.
Pusset M.
Pusset J.
Laboute P.
Tetrahedron
1985,
41:
6019
13a Fedoreyev SA.
Utkina NK.
Il’yin SG.
Reshetnyak MV.
Maximov OB.
Tetrahedron Lett.
1986,
27:
3177
13b Tsukamoto S.
Tane K.
Ohta T.
Matsunaga S.
Fusetani N.
van Soest RWM.
J. Nat. Prod.
2001,
64:
1576
13c Assmann M.
van Soest RWM.
Köck M.
J. Nat. Prod.
2001,
64:
1345
13d Goetz GH.
Harrigan GG.
Likos J.
J. Nat. Prod.
2001,
64:
1581
13e Assmann M.
Köck M.
Z. Naturforsch. C: Biosci.
2002,
57:
153
14a Walker RP.
Faulkner DJ.
Van Engen D.
Clardy J.
J. Am. Chem. Soc.
1981,
103:
6772
14b Braekman JC.
Daloze D.
Moussiaux B.
Stoller C.
Deneubourg F.
Pure Appl. Chem.
1989,
61:
509
14c Keifer PA.
Schwartz RE.
Koker MES.
Hughes RG.
Rittschof D.
Rinehart KL.
J. Org. Chem.
1991,
56:
2965
14d Kobayashi J.
Tsuda M.
Ohizumi Y.
Experientia
1991,
47:
301
14e Shen X.
Perry TL.
Dunbar CD.
Kelly-Borges M.
Hamann MT.
J. Nat. Prod.
1998,
61:
1302
14f Eder C.
Proksch P.
Wray V.
vanSoest RWM.
Ferdinandus E.
Pattisina LA.
Sudarsono .
J.Nat. Prod.
1999,
62:
1295
15 Tuskamoto S.
Kato H.
Hirota H.
Fusetani N.
J. Nat. Prod.
1996,
59:
501
16a Kobayashi J.
Tsuda M.
Murayama T.
Nakamura H.
Ohizumi Y.
Ishibashi M.
Iwamura M.
Ohta T.
Nozoe S.
Tetrahedron
1990,
46:
5579
16b Williams DH.
Faulkner DJ.
Tetrahedron
1996,
52:
5381
16c Assmann M.
Köck M.
Z. Naturforsch., C: Biosci.
2002,
57:
157
17 Urban S.
Leone P.
Carroll AR.
Fechner GA.
Smith J.
Hooper JNA.
Quinn RJ.
J. Org. Chem.
1999,
64:
731
18 Ciminiello P.
Dell’Aversano C.
Fattorusso E.
Magno S.
Eur. J. Org.Chem.
2001,
55
19a Kinnel RB.
Gehrken H.-P.
Scheuer PJ.
J. Am. Chem. Soc.
1993,
115:
3376
19b Kobayashi J.
Suzuki M.
Tsuda M.
Tetrahedron
1997,
53:
15681
19c Kinnel RB.
Gehrken H.-P.
Swali R.
Skoropowski G.
Scheuer PJ.
J. Org. Chem.
1998,
63:
3281
20 Kato T.
Shizuri Y.
Izumida H.
Yokoyama A.
Endo M.
TetrahedronLett.
1995,
36:
2133
21a Gunasekera SP.
Cranick S.
Longley RE.
J. Nat. Prod.
1989,
52:
757
21b Cafieri F.
Fattorusso E.
Mangoni A.
Taglialatela-Scafati O.
Tetrahedron Lett.
1995,
36:
7893
21c Mancini I.
Guella G.
Amade P.
Roussakis C.
Pietra F.
TetrahedronLett.
1997,
38:
6271
21d Umeyama A.
Ito S.
Yuasa E.
Arihara S.
Yamada T.
J. Nat. Prod.
1998,
61:
1433
21e Cafieri F.
Fattorusso E.
Taglialatela-Scafati O.
J.Nat. Prod.
1998,
61:
122
21f König GM.
Wright AD.
Linden A.
Planta Med.
1998,
64:
443
21g Reddy NS.
Venkateswarlu Y.
Biochem.Syst. Ecol.
2000,
28:
1035
21h Reddy NS.
Venkateswarlu Y.
IndianJ. Chem., Sect. B
2000,
39:
971
22a Ahond A.
Bedoya-Zurita M.
Colin M.
Fizames C.
Laboute P.
Lavelle F.
Laurent D.
Poupat C.
Pusset J.
Pusset M.
Thoison O.
Potier P.
C.R. Acad. Sci. Paris
1988,
307:
145
22b Wright AE.
Chiles SA.
Cross SS.
J. Nat. Prod.
1991,
54:
1684
23 Van Pee K.-H.
Arch.Microbiol.
2001,
175:
250
24 Andrade P.
Willoughby R.
Pomponi SA.
Kerr RG.
Tetrahedron Lett.
1999,
40:
4775
25 Cafieri F.
Fattorusso E.
Mangoni A.
Taglialatela-Scafati O.
Tetrahedron
1996,
52:
13713
26 Braekman J.-C.
Daloze D.
Stoller C.
van Soest RWM.
Biochem.Syst. Ecol.
1992,
20:
417
27 Assmann M.
Lichte E.
von Soest RWM.
Köck M.
Org.Lett.
1999,
1:
455
28 Lindel T.
Hochgürtel M.
Assmann M.
Köck M.
J. Nat. Prod.
2000,
63:
1566
29 Rodríguez AD.
Piña IC.
J.Nat. Prod.
1993,
56:
907
30a Horii S.
Kameda Y.
J.Antibiot.
1968,
21:
665
30b Hatano K.
Nogami I.
Higashide E.
Kishi T.
Agric. Biol. Chem.
1984,
48:
1503
30c Garcia A.
Vazquez MJ.
Quiñoa E.
Riguera R.
Debitus C.
J. Nat. Prod.
1996,
59:
782
30d Hemscheidt T.
Burgoyne DL.
Moore RE.
J. Chem. Soc., Chem. Commun.
1995,
205
31 Bailey DM.
Johnson RE.
J. Med. Chem.
1973,
16:
1300
32 Friedel, M.; Lindel, T. 2002 , unpublished.
33 Storey BT.
Sullivan WW.
Moter CL.
J. Org. Chem.
1964,
29:
3118
34 Sharma G.
Magdoff-Fairchild B.
J. Org. Chem.
1977,
42:
4118
35 Rogers RS.
Rapoport H.
J. Am. Chem. Soc.
1980,
102:
7335
36 Marques MA.
Doss RM.
Urbach AR.
Dervan PB.
Helv. Chim. Acta
2002,
85:
4485 ; and ref. cited therein
37 Rosa R.
Silva W.
Escalona de Motta G.
Rodriguez AD.
Morales JJ.
Ortiz M.
Experientia
1992,
42:
885
38 Kobayashi J.
Nakamura H.
Ohizumi Y.
Experientia
1988,
38:
86
39 Schrader TH.
TetrahedronLett.
1998,
39:
517
40 Colson G.
Rabault B.
Lavelle F.
Zerial A.
Biochem. Pharmacol.
1992,
43:
1717
41 Meijer L.
Thunnissen A.-MWH.
White AW.
Garnier M.
Nikolic M.
Tsai L.-H.
Walter J.
Cleverley KE.
Salinas PC.
Wu Y.-Z.
Biernat J.
Mandelkow E.-M.
Kim S.-H.
Pettit GR.
Chem.Biol.
2000,
7:
51
42 Curman D.
Cinel B.
Williams DE.
Rundle N.
Block WD.
Goodarzi AA.
Hutchins JR.
Clarke PR.
Zhou B.-B.
Lees-Miller SP.
Andersen RJ.
Roberge M.
J. Biol.Chem.
2001,
276:
17914
43 Tasdemir D.
Mallon R.
Greenstein M.
Feldberg LR.
Kim SC.
Collins K.
Wojciechowicz D.
Mangalindan GC.
Concepción GP.
Harper MK.
Ireland CM.
J. Med.Chem.
2002,
45:
529
44 Vassas A.
Bourdy G.
Paillard JJ.
Lavayre J.
Pais M.
Quirion JC.
Debitus C.
PlantaMed.
1996,
62:
28
45 Breton JJ.
Chabot-Fletcher MC.
J. Pharmacol.Exp. Ther.
1997,
282:
459
46 Roshak A.
Jackson JR.
Chabot-Fletcher MC.
Marshall LA.
J.Pharmacol. Exp. Ther.
1997,
283:
955
47 48
49a Badger AM.
Cook MN.
Swift BA.
Newman-Tarr TM.
Gowen M.
Lark M.
J.Pharmcol. Exp. Ther.
1999,
290:
587
49b
50a Chanas B.
Pawlik JR.
Lindel T.
Fenical W.
J.Exp. Mar. Biol. Ecol.
1996,
208:
185
50b Wilson DM.
Puyana M.
Fenical W.
Pawlik JR.
J.Chem. Ecol.
1999,
25:
2811
50c Assmann M.
Lichte E.
Pawlik JR.
Köck M.
Mar. Ecol.: Prog. Ser.
2000,
207:
255
51 Lindel T.
Hoffmann H.
Hochgürtel M.
Pawlik JR.
J. Chem. Ecol.
2000,
26:
1477
52 Turnbull K.
Prog.Heterocycl. Chem.
1998,
10:
153 ;and ref. cited therein.
53 Cavalleri B.
Volpe G.
Rosselli del Turco B.
Diena A.
Farmaco
1976,
31:
393
54 Abas SA.
Hossain MB.
van der Helm D.
Schmitz FJ.
Laney M.
Cabuslay R.
Schatzman RC.
J.Org. Chem.
1996,
61:
2709
55 Radchenko OS.
Novikov VL.
Willis RH.
Murphy PT.
Elyakov GB.
Tetrahedron Lett.
1997,
38:
3581
56 Xu Y.-Z.
Yakushijin K.
Horne DA.
TetrahedronLett.
1993,
34:
6981
57 Wan Z.-K.
Woo GHC.
Snyder JK.
Tetrahedron
2001,
57:
5497
58 Little TL.
Webber SE.
J. Org. Chem.
1994,
59:
7299
59 Bolton JL.
McClelland RA.
J. Am. Chem. Soc.
1989,
111:
8172 ; and ref. cited therein.
60 Colvin ME.
Seidl ET.
Nielsen IMB.
Le Bui L.
Hatch FT.
Chem.-Biol. Interact.
1997,
108:
39
61a Braun M.
Büchi G.
J.Am. Chem. Soc.
1976,
98:
3049
61b Braun M.
Büchi G.
Bushey DF.
J.Am. Chem. Soc.
1978,
100:
4208
62a Xu Y.-Z.
Yakushijin K.
Horne DA.
Tetrahedron Lett.
1992,
33:
4285
62b Xu Y.-Z.
Yakushijin K.
Horne DA.
J.Org. Chem.
1996,
61:
9569
63a Banfield JE.
McGuinness DS.
J. Chem. Soc.
1963,
2747
63b Gompper R.
Bichlmayer K.
Angew. Chem., Int. Ed. Engl.
1979,
18:
156 ; Angew. Chem. 1979 , 91 , 170
63c Biswas KM.
Mallik H.
Phytochemistry
1986,
25:
1727
63d Prager RH.
Tsopelas C.
Aust. J.Chem.
1990,
43:
367
64 Fernandez JJ.
Souto ML.
Daranas AH.
Norte M.
Curr. Top.Phytochem.
2000,
4:
105
65a Walters MA.
Lee MD.
TetrahedronLett.
1994,
35:
8307
65b Deghati PYF.
Wanner MJ.
Koomen GJ.
Tetrahedron Lett.
1998,
39:
4561
65c Lovely CJ.
Du H.
Rasika Dias HV.
Org. Lett.
2001,
3:
1319
66 D’Auria M.
Racioppi R.
J. Photochem. Photobiol.,A
1998,
112:
145
67a Mohammad T.
Morrison H.
HogenEsch H.
Photochem. Photobiol.
1999,
69:
115 ; and ref. cited therein
67b Haralampus-Grynaviski N.
Ransom C.
Ye T.
Rozanowska M.
Wrona M.
Sarna T.
Simon JD.
J.Am. Chem. Soc.
2002,
124:
3461
68 Kosaka K.
Maruyama K.
Nakamura H.
Ikeda M.
J. Heterocyclic Chem.
1991,
28:
1941
69a Richard JP.
Szymanski P.
Williams KB.
J. Am. Chem. Soc.
1998,
120:
10372
69b Mayr H.
Kempf B.
Ofial AR.
Acc.Chem. Res.
2003,
36:
66 ;and ref. cited therein
70 Brimble MA.
Brimble MT.
Hodges R.
Lane GA.
Aust. J. Chem.
1988,
41:
1583
71a Marchais S.
Al Mourabit A.
Ahond A.
Poupat C.
Potier P.
Tetrahedron Lett.
1999,
40:
5519
71b Banwell MG.
Bray AM.
Willis AC.
Wong DJ.
NewJ. Chem.
1999,
23:
687
72 Lindel T.
Hoffmann H.
Liebigs Ann./Recueil
1997,
1525
73 Sosa ACB.
Yakushijin K.
Horne DA.
Tetrahedron Lett.
2000,
41:
4295
74 Cho M.
Matsuki S.
Mizuno A.
Annoura H.
Tatsuoka T.
J. Heterocycl.Chem.
1997,
34:
87
75 De Nanteuil G.
Ahond A.
Poupat C.
Thoison O.
Potier P.
Bull. Soc.Chim. Fr.
1986,
813
76a Daninos S.
Al Mourabit A.
Ahond A.
Bedoya-Zurita M.
Poupat C.
Potier P.
Bull.Soc. Chim. Fr.
1994,
131:
590
76b Daninos-Zeghal S.
Al Mourabit A.
Ahond A.
Poupat C.
Potier P.
Tetrahedron
1997,
53:
7605
77a Schweizer EE.
J. Am. Chem. Soc.
1964,
86:
2744
77b Schweizer EE.
Smucker LD.
Votral RJ.
J. Org. Chem.
1966,
31:
467
78a Fargher RG.
Pyman FL.
J. Chem. Soc.
1919,
115:
217
78b Weinmann H.
Harre M.
Koenig K.
Merten E.
Tilstam U.
TetrahedronLett.
2002,
43:
593 ;and ref. cited therein
79 Narasimham NS.
Ammanamanchi R.
Tetrahedron Lett.
1983,
23:
4733
80a Lindel T.
Hochgürtel M.
TetrahedronLett.
1998,
39:
2541
80b Lindel T.
Hochgürtel M.
J. Org. Chem.
2000,
65:
2806
81a Sonogashira K.
Tohda Y.
Hagihara N.
Tetrahedron Lett.
1975,
16:
4467
81b Sakamoto T.
Nagata H.
Yoshinori K.
Shiraiwa M.
Yamanaka H.
Chem. Pharm. Bull.
1987,
35:
823
82 Kirk KL.
J.Heterocycl. Chem.
1985,
22:
57
83a Cliff MD.
Pyne SG.
J.Org. Chem.
1995,
60:
2378
83b Cliff MD.
Pyne SG.
Tetrahedron
1996,
52:
13703
83c Cliff MD.
Pyne SG.
J.Org. Chem.
1997,
62:
1023
84 Casara P.
Danzin C.
Metcalf B.
Jung M.
J. Chem. Soc., Perkin Trans. 1
1985,
2201
85 Breckle, G.; Polborn, K.; Lindel,T. Z. Naturforsch. B.: Chem. Sci. 2003 , 58 , 451.
86 Berrée F.
Girard-Le Bleis P.
Carboni B.
Tetrahedron Lett.
2002,
43:
4935
87 Meanwell NA.
Roth HR.
Smith ECR.
Wedding DL.
Wright JJK.
J. Org. Chem.
1991,
56:
6897
88 Lindel T.
Hoffmann H.
Tetrahedron Lett.
1997,
38:
8935
89a Roue N.
Bergman J.
Tetrahedron
1999,
55:
14729
89b Davis RA.
Aalbersberg W.
Meo S.
da Rocha RM.
Ireland CM.
Tetrahedron
2002,
58:
3263
90a Bedoya-Zurita M.
Ahond A.
Poupat C.
Potier P.
Tetrahedron
1989,
45:
6713
90b Ahond A.
Al Mourabit A.
Bedoya-Zurita M.
Heng R.
Marques Braga R.
Poupat C.
Potier P.
Tetrahedron
1992,
48:
4327
91a Commerçon A.
Ponsinet G.
TetrahedronLett.
1990,
31:
3871
91b Commerçon A.
Guérémy C.
Tetrahedron Lett.
1991,
32:
1419
92 Commerçon A.
Paris JM.
Tetrahedron Lett.
1991,
32:
4905
93 Griffith RK.
Pietro DA.
Synthesis
1983,
576
94 Bott K.
Chem.Ber.
1973,
106:
2513
95 Marchais S.
Al Mourabit A.
Ahond A.
Poupat C.
Potier P.
TetrahedronLett.
1998,
39:
8085
96 Foley LH.
Büchi G.
J. Am. Chem. Soc.
1982,
104:
1776
97 Olofson A.
Yakushijin K.
Horne DA.
J.Org. Chem.
1998,
63:
1248
98a Akabori S.
Chem. Ber.
1933,
66:
151
98b Lawson A.
Morley HV.
J. Chem. Soc.
1955,
1695
99 Fresneda PM.
Molina P.
Sanz MA.
TetrahedronLett.
2001,
42:
851
100a Jiang B.
Liu J.-F.
Zhao S.-Y.
Org. Lett.
2001,
3:
4011
100b Jiang B.
Liu J.-F.
Zhao S.-Y.
Org.Lett.
2002,
4:
3951
101 Gurjar MK.
Bera S.
Org. Lett.
2002,
4:
3569
102 Wiese KJ.
Yakushijin K.
Horne DA.
TetrahedronLett.
2002,
43:
5135
103 Lindel T.
Hoffmann H.
Hochgürtel M. In
Bioorganic Chemistry - Highlightsand New Aspects Diederichsen U., Lindhorst T. K., WestermannB., Wessjohann L. A.
Wiley-VCH;
Weinheim:
1999.
p.8-17
104 Sosa ACB.
Yakushijin K.
Horne DA.
J. Org. Chem.
2002,
67:
4498
105 Sosa ACB.
Yakushijin K.
Horne DA.
Org. Lett.
2000,
2:
3443
106 Xu Y.-Z.
Yakushijin K.
Horne DA.
TetrahedronLett.
1996,
37:
8121
107 Xu Y.-Z.
Yakushijin K.
Horne DA.
J.Org. Chem.
1997,
62:
456
108 Sosa ACB.
Yakushijin K.
Horne DA.
J. Org. Chem.
2000,
65:
610
109 D’Ambrosio M.
Guerriero A.
Ripamonti M.
Debitus C.
Waikedre J.
Pietra F.
Helv. Chim. Acta
1996,
79:
727
110 Olofson A.
Yakushijin K.
Horne DA.
J.Org. Chem.
1997,
62:
7918
111 Kawasaki I.
Sakaguchi N.
Fukushima N.
Fujioka N.
Nikaido F.
Yamashita M.
Ohta S.
TetrahedronLett.
2002,
43:
4377
112 Back TG.
Baron DL.
Yang K.
J.Org. Chem.
1993,
58:
2407 ;and references cited therein.
113 Dilley AS.
Romo D.
Org. Lett.
2001,
3:
1535
114 Xu Y.-Z.
Phan G.
Yakushijin K.
Horne DA.
Tetrahedron Lett.
1994,
35:
351
115 Annoura H.
Tatsuoka T.
Tetrahedron Lett.
1995,
36:
413
116 Davis FA.
Vishwakarma LC.
Billmers JM.
Finn J.
J. Org. Chem.
1984,
49:
3241
117a Anderson GT.
Chase CE.
Koh Y.
Stien D.
Weinreb SM.
Shang M.
J.Org. Chem.
1998,
63:
7594
117b Stien D.
Anderson GT.
Chase CE.
Koh Y.
Weinreb SM.
J. Am. Chem. Soc.
1999,
121:
9574
118 Baron E.
O’Brien P.
Towers TD.
Tetrahedron Lett.
2002,
43:
723
119a Sharpless KB.
Hori T.
J.Org. Chem.
1976,
41:
176
119b Bussas R.
Kresze G.
Liebigs Ann. Chem.
1980,
629
120a Feldman KS.
Saunders JC.
J. Am. Chem. Soc.
2002,
124:
9060
120b Feldman KS.
Saunders JC.
Wrobleski ML.
J. Org. Chem.
2002,
67:
7096
121a Stang PJ.
Zhdankin VV.
J. Am. Chem. Soc.
1991,
113:
4571
121b Zhdankin VV.
Stang PJ.
Tetrahedron
1998,
54:
10927
122a Overman LE.
Rogers BN.
Tellew JE.
Trenkle WC.
J. Am. Chem. Soc.
1997,
119:
7159
122b Bélanger G.
Hong F.-T.
Overman LE.
Rogers BN.
Tellew JE.
Trenkle WC.
J. Org. Chem.
2002,
67:
7880
123 Poullennec KG.
Kelly AT.
Romo D.
Org.Lett.
2002,
4:
2645
124 Jacquot DEN.
Hoffmann H.
Polborn K.
Lindel T.
TetrahedronLett.
2002,
43:
3699
125 Frigerio M.
Santagostino M.
Tetrahedron Lett.
1994,
35:
8019
126 Jacquot, D. E. N.; Lindel, T. 2002 , unpublished.
127 Jacquot, D. E. N.; Lindel, T. 2002 , in preparation.
128a Barani M.
Fioravanti S.
Pellacani L.
Tardella PA.
Tetrahedron
1994,
50:
11235
128b Felice E.
Fioravanti S.
Pellacani L.
Tardella PA.
Tetrahedron Lett.
1999,
40:
4413
128c Fioravanti S.
Morreale A.
Pellacani L.
Tardella PA.
Synthesis
2002,
1975
129 Starr JT.
Koch G.
Carreira EM.
J.Am. Chem. Soc.
2000,
122:
8793
130 Bolm C.
Gerlach A.
Dinter CL.
Synlett
1999,
195
131a Giordan M.
Custodio R.
Trigo JR.
J.Comput. Chem.
1996,
17:
156
131b Giordan M.
J.Comput. Chem.
1998,
19:
1853
132 Meyer, A.; Lindel, T. 2002 ,unpublished.
133 Poullennec KG.
Romo D.
J. Am. Chem. Soc.
2003,
125:
6344
134 Pallai P.
Goodman M.
J. Chem. Soc., Chem. Commun.
1982,
5:
280
135 König SG.
Miller SM.
Leonard KA.
Löwe RS.
Chen BC.
Austin DJ.
Org.Lett.
2003,
5:
2203
