Abstract
A survey through the synthetic possibilities of pentalongin and its derivatives is presented. Pentalongin is the parent compound in the 3,4-dehydropyranonaphthoquinone series and is the active principle of the medicinal plant Pentas longiflora . Attention is paid to eight approaches towards these 3,4-dehydropyranonaphthoquinones. Synthetic methodologies for the corresponding nitrogen analogues are described, focusing on several natural products.
1 Historical Background
2 Isolation of Pyranonaphthoquinone Antibiotics
2.1 Isolation of Pentalongin
2.2 Isolation of Related Naphthoquinones
2.3 Stability of Pentalongin
3 Pyranonaphthoquinone Antibiotics
4 Evaluation of Synthetic Strategies towards Pentalongin
4.1 Retrosynthetic Analysis
4.2 Base-Induced Intramolecular Cyclization (A )
4.3 Acid-Induced Cyclization (B )
4.4 Friedel-Crafts Cyclization (C )
4.5 Lemieux-Johnson Oxidation of 2-Allyl-1,4-naphthoquinone (D )
4.6 Ring Closure via Lactonization (E )
4.7 Ring Closure Using Grubbs’ Methodology (F )
4.8 Heck Cyclization (G )
4.9 Phthalide-Coupling Reaction (H )
5 Nitrogen Analogues of Pentalongin
5.1 Occurrence and Bioactivity
5.2 Synthetic Approaches towards 2-Aza-anthraquinones
6 Other Isolated Quinones and Syntheses Thereof
6.1 Synthesis of Harounoside
6.2 Synthesis of Isagarin
6.3 Synthesis of 2-Alkoxymethyl-3-trifluoromethyl-1,4-naphthoquinones
7 Concluding Remarks
Key words
quinones - natural products - heterocycles - pentalongin - 2-aza-anthraquinones
References and Notes 1 Present adress: Institute of Chemistry, Vietnamese Academy for Sciences and Technology, 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam
2 Rahman A.-U.
Studies in Natural Products Chemistry
1990,
7:
405
3 Flore des Plantes Ligneuses du Rwanda, Spermatophytes
Vol. 3:
Troupin CG.
Institut National de Recherche Scientifique;
Butare:
1985.
4 Van Puyvelde L.
Ph.D. Thesis
Leiden University;
The Netherlands:
1988.
5 Flore des Plantes Ligneuses du Rwanda, Spermatophytes
Vol 3:
Troupin CG.
Institut National de Recherche Scientifique;
Butare:
1985.
p.196
6 Medicinal Plants of East-Africa
Kokwaro JO.
East African Literature Bureau;
Dar Es Salaam:
1976.
p.190
7 De Kimpe N.
Van Puyvelde L.
Schripsema J.
Erkelens C.
Verpoorte R.
Magn. Reson. Chem.
1993,
31:
329-330
8 Hari L.
De Buyck LF.
De Pooter HL.
Phytochemistry
1991,
30:
1726
9 Wanyoike GN.
Chhabra SC.
Lang’at-Thoruwa CC.
Omar SA.
J. Ethnopharmacol.
2004,
90:
129
10 Van Puyvelde L.
Ntawukiliyayo JD.
Portaels F.
Hakizamungu E.
Phytother. Res.
1994,
8:
65
11 Itokawa H.
Ibrahim Z.
Qiao YF.
Takeya K.
Chem. Pharm. Bull.
1993,
41:
1869
12 Heide L.
Leistner E.
J. Chem. Soc., Chem. Commun.
1981,
334
13 Itokawa H.
Qiao Y.
Takeya K.
Phytochemistry
1991,
30:
637
14 Van Puyvelde L.
El-Hady S.
De Kimpe N.
Feneau-Dupont J.
Declercq J.-P.
J. Nat. Prod.
1998,
61:
1020
15 El-Hady S.
Bukuru J.
Kesteleyn B.
Van Puyvelde L.
Nguyen Van T.
De Kimpe N.
J. Nat. Prod.
2002,
65:
1377
16a Mechoulam R.
Gaoni Y.
Fortschr. Chem. Org. Naturst.
1967,
25:
175
16b Claussen U.
von Spulak F.
Korte F.
Tetrahedron
1968,
24:
1021
17a Kureel SP.
Kapil RS.
Popli SP.
Tetrahedron Lett.
1969,
3857
17b Begley MJ.
Clarke DG.
Crombie L.
Whiting DA.
J. Chem. Soc., Chem. Commun.
1970,
1547
18 Bukuru J.
Nguyen Van T.
Van Puyvelde L.
He W.
De Kimpe N.
Tetrahedron
2003,
59:
5905
19 Claessens S.
Verniest G.
El-Hady S.
Nguyen VT.
Kesteleyn B.
Van Puyvelde L.
De Kimpe N.
Tetrahedron
2006,
62:
5252
20 The Anomeric Effect and Related Stereoelectronic Effects at Oxygen
Kirby AJ.
Springer;
New York:
1983.
21 Thomson RH.
Naturally Occurring Quinones
2nd ed:
Academic Press Inc.;
New York:
1971.
22 Naruta Y.
Maruyama K.
Recent Advances in the Synthesis of Quinonoid Compounds, In The Chemistry of Quinonoid Compounds
Vol. 2:
Patai S.
Rappoport Z.
John Wiley;
New York:
1998.
p.241
23 Moore HW.
Science
1977,
197:
527
24 Brimble MA.
Nairn M.
Prabaharan H.
Tetrahedron
2000,
56:
1937
25a Kadkol MV.
Gopalkrishnan KS.
Narasimhachari N.
J. Antibiot.
1971,
24:
245
25b Nagarajan R.
Narasimhachari N.
Kadkol MV.
Gopalkrishnan KS.
J. Antibiot.
1971,
24:
249
25c Narasimhachari N.
Gopalkrishnan KS.
J. Antibiot.
1974,
27:
283
25d Thines E.
Anke H.
Sterner O.
J. Nat. Prod.
1998,
61:
306
26a Ruelius HW.
Gauhe A.
Ann. Chem.
1950,
569:
38
26b Parisot D.
Devys M.
Férézou J.-P.
Barbier M.
Phytochemistry
1983,
22:
1301
26c Parisot D.
Devys M.
Barbier M.
Phytochemistry
1989,
28:
3240
27 Otake N, Seto H, Kyo B, Shu H, To T, Mochizuki J, and Hayakawa Y. inventors; Jpn. Kokai Tokkyo Koho, JP 01290673 [89290673].
; Chem. Abstr. 1990 , 113 , 38905
28a Wang W.
Breining T.
Li T.
Milburn R.
Attardo G.
Tetrahedron Lett.
1998,
39:
2459
28b Wang W.
Li T.
Milburn R.
Yates J.
Hinnant E.
Luzzio MJ.
Noble SA.
Attardo G.
Bioorg. Med. Chem. Lett.
1998,
8:
1579
29 Naito T.
Makita Y.
Yazaki S.
Kaneko C.
Chem. Pharm. Bull.
1986,
34:
1505
30 Hayashi T.
Smith FT.
Lee KH.
J. Med. Chem.
1987,
30:
2005
31a Kobayashi K.
Uchida M.
Uneda T.
Tanmatsu M.
Morikawa O.
Konishi H.
Tetrahedron Lett.
1998,
39:
7725
31b Kobayashi K.
Uchida M.
Uneda T.
Yoneda K.
Tanmatsu M.
Morikawa O.
Konishi H.
J. Chem. Soc., Perkin Trans. 1
2001,
2977
31c Kobayashi K.
J. Synth. Org. Chem. Jpn.
2004,
62:
811
32 Aldersley MF.
Dean FM.
Nayyir-Mahzir R.
J. Chem. Soc., Perkin Trans. 1
1983,
1753
33 Aldersley MF.
Chisti SH.
Dean FM.
Douglas ME.
Ennis DS.
J. Chem. Soc., Perkin Trans. 1
1990,
2163
34 Wilson RM.
Wunderly SW.
Walsh TF.
Musser AK.
Outcalt R.
Geiser F.
Gee SK.
Brabender W.
Yerino L.
Conrad TT.
Tharp GA.
J. Am. Chem. Soc.
1982,
104:
4429
35 Joshi BS.
Jiang Q.
Rho T.
Pelletier S.
J. Org. Chem.
1994,
59:
8220
36 Kesteleyn B.
De Kimpe N.
Van Puyvelde L.
J. Org. Chem.
1999,
64:
1173
37 Syper L.
Mlocowski J.
Kloc K.
Tetrahedron
1983,
39:
781
38 Hayashi T.
Smith FT.
Lee KH.
J. Med. Chem.
1987,
30:
2005
39 Pialat JP.
Hoffmann P.
Moulis C.
Fouraste I.
Labidalle S.
Nat. Prod. Lett.
1998,
12:
23
40 Kesteleyn B.
De Kimpe N.
Van Puyvelde L.
Synthesis
1999,
1881
41 Nguyen Van T.
De Kimpe N.
Tetrahedron Lett.
2004,
45:
3443
42a Clark JS.
Kettle JG.
Tetrahedron Lett.
1997,
38:
123
42b Clark JS.
Kettle JG.
Tetrahedron Lett.
1997,
39:
127
42c Fujimura O.
Fu GC.
Grubbs RH.
J. Org. Chem.
1994,
59:
4029
42d Gurjar MK.
Krishna LM.
Reddy BS.
Chorghade MS.
Synthesis
2000,
557
42e Chatterjee AK.
Morgan JP.
Scholl M.
Grubbs RH.
J. Am. Chem. Soc.
2002,
122:
3783
43 Sturino CF.
Wong JCY.
Tetrahedron Lett.
1998,
39:
9623
44 Giles RGF.
Green IR.
Taylor CP.
Tetrahedron Lett.
1999,
40:
4871
45 Adams R.
Geissman TA.
Baker BR.
Teeter HM.
J. Am. Chem. Soc.
1941,
63:
528
46 Liebeskind LS.
Riesinger SW.
J. Org. Chem.
1993,
58:
408
47 Knolker HJ.
Frohner W.
J. Chem. Soc., Perkin Trans. 1
1998,
173
48 Chang HX.
Chou TC.
Savaraj N.
Liu LF.
Yu C.
Cheng CC.
J. Med. Chem.
1999,
42:
405
49 Nguyen Van T.
De Kimpe N.
Tetrahedron
2003,
5941
50 Claessens S.
Naidoo D.
Mulholland D.
Verschaeve L.
Van Staden J.
De Kimpe N.
Synlett
2006,
621
51a Kraus GA.
Sugimoti H.
Tetrahedron Lett.
1978,
2263
51b Kraus GA.
Cho H.
Crowley S.
Roth B.
Sugimoto H.
Prugh S.
J. Org. Chem.
1983,
48:
3499
52a Hauser FM.
Mal D.
J. Am. Chem. Soc.
1983,
105:
5688
52b Hauser FM.
Rhee RP.
J. Org. Chem.
1978,
43:
178
52c Hauser FM.
Rhee RP.
J. Am. Chem. Soc.
1979,
101:
1628
53a Cossy J.
Taillier C.
Bellosta V.
Tetrahedron Lett.
2002,
43:
7263
53b Eiden F.
Wanner KT.
Arch. Pharm.
1985,
548
54 Giles RGF.
Green IR.
Taylor CP.
Tetrahedron Lett.
1999,
40:
4871
55 Hamilton MA.
Knorr MS.
Cajori FA.
Antibiot. Chemother.
1953,
3:
853
56 Arsenault GP.
Tetrahedron Lett.
1965,
45:
4033
57 Parisot D.
Devys M.
Barbier M.
J. Antibiot.
1989,
42:
1189
58 Steyn PS.
Wessels PL.
Marasas WFO.
Tetrahedron
1979,
35:
1551
59 Visconti A.
Surico G.
Iacobellis NS.
Bottalico A.
Phytopathol. Mediterr.
1983,
22:
152
60 Parisot D.
Devys M.
Barbier M.
Z. Naturforsch.
1989,
44:
1473
61 Parisot D.
Devys M.
Barbier M.
Phytochemistry
1990,
29:
3364
62 Gräfe U.
Ihn W.
Tresselt D.
Miosga N.
Kaden U.
Schlegel B.
Bormann E.-J.
Sedmera P.
Novak J.
BioMetals
1990,
3:
39
63 Gräfe U.
Roemer W.
Pharmazie
1991,
46:
297
64 Okunade AL.
Clark AM.
Hufford CD.
Oguntimein BO.
Planta Med.
1999,
65:
447
65 Nok A.
J. Cell Biochem. Funct.
2002,
20:
205
66a Walton BT.
Ho C.
Ma CY.
O’Neil EG.
Kao GL.
Science
1983,
222:
422
66b Ma CY.
Ho C.
Walton BT.
Kao GL.
Guerin MR.
Environ. Sci. Technol.
1984,
18:
362
67 Solis PN.
Lang’at C.
Gupta MP.
Kirby GC.
Warhurst DC.
Philipson JD.
Planta Med.
1995,
61:
62
68 Moriyasu Y.
Miyagawa H.
Hamada N.
Miyawaki H.
Ueno T.
Phytochemistry
2001,
58:
239
69 Miljkovic A.
Mantle PG.
Williams DJ.
Rassing B.
J. Nat. Prod.
2001,
64:
1251
70 Werner W, and Gräfe U. inventors; DE 4231632 A1 1990324.
; Chem. Abstr. 1994 , 120 , 323279
71 Koyama J.
Morita I.
Kobayashi N.
Osakai T.
Usuki Y.
Taniguchi M.
Bioorg. Med. Chem. Lett.
2005,
15:
1079
72 Khanapure SP.
Biehl ER.
Heterocycles
1988,
27:
2643
73 Bolognese A.
Correale G.
Manfra M.
Lavecchia A.
Novellino E.
Barone V.
Tetrahedron
2004,
60:
8189 ; and cited references
74 Koyama J.
Morita I.
Kobayashi N.
Osakai T.
Hotta H.
Takayasu J.
Nishino H.
Tokuda H.
Cancer Lett. (Amsterdam, Neth.)
2004,
212:
1
75 Krapcho AP.
Menta E.
Oliva A.
Di Domenico R.
Fiocchi L.
Maresch ME.
Gallagher CE.
Hacker MP.
Beggiolin G.
Giuliani FC.
Pezzoni G.
Spinelli S.
J. Med. Chem.
1998,
41:
5429
76 Faivre S.
Raymond R.
Boige V.
Gatineau M.
Buthaut X.
Rixe O.
Bernareggi A.
Camboni G.
Armand J.-P.
Clin. Cancer Res.
2001,
7:
43
77 Burckhardt G.
Walter A.
Triebel H.
Storl K.
Simon H.
Storl J.
Opitz A.
Roemer E.
Zimmer C.
Biochemistry
1998,
37:
4703
78 Gonsette RE.
J. Neurosci.
2004,
223:
81
79 Cavaletti G.
Cavaletti E.
Crippa L.
Di Luccio E.
Oggioni N.
Mazzanti B.
Biagiolo T.
Sala F.
Frigo M.
Rota S.
Tagliabue E.
Stanzani L.
Galbiati S.
Rigolio R.
Zoia C.
Tredici G.
Perseghin P.
Dassi M.
Riccio P.
Lolli F.
J. Neuroimmunol.
2004,
151:
55
80 Gomez-Monterrey I.
Campiglia P.
Grieco P.
Diurno MV.
Bolognese A.
La Colla P.
Novellino E.
Bioorg. Med. Chem.
2003,
11:
3769
81 Croisy-Delcey M.
Heul C.
Bisagni E.
J. Heterocycl. Chem.
1988,
25:
661
82 Ohgaki E.
Motoyoshiya J.
Narita S.
Kakurai T.
Hayashi S.
Hirakawa K.
J. Chem. Soc., Perkin Trans. 1
1990,
3109
83a Potts KT.
Bhattacharjee D.
Walsh EB.
J. Chem. Soc., Chem. Commun.
1984,
114
83b Potts KT.
Bhattacharjee D.
Walsh EB.
J. Org. Chem.
1986,
51:
2011
84a Cameron DW.
Deutscher KR.
Feutrill GI.
Tetrahedron Lett.
1980,
21:
5089
84b Cameron DW.
Deutscher KR.
Feutrill GI.
Aust. J. Chem.
1982,
35:
1439
85 Collet SC.
Rémi J.-F.
Cariou C.
La& iuml;b S.
Guingant AY.
Quang Vu N.
Dujardin G.
Tetrahedron Lett.
2004,
45:
4911
86 Gomez-Monterrey IM.
Campiglia P.
Mazzoni O.
Novellino E.
Diurno MV.
Tetrahedron Lett.
2001,
42:
5755
87 Bondock S.
Heteroat. Chem.
2005,
16:
49
88 Sartori G.
Casnati G.
Bigi F.
Robles P.
Tetrahedron Lett.
1987,
28:
1533
89 Cameron DW.
Deutscher KR.
Feutrill GI.
Hunt DE.
Aust. J. Chem.
1982,
35:
1451 ; and cited references therein
90 Watanabe M.
Shinoda E.
Shimizu Y.
Furukawa S.
Tetrahedron
1987,
43:
5281
91 Werner W.
Gräfe U.
Ihn W.
Tresselt D.
Winter S.
Paulus E.
Tetrahedron
1997,
53:
109
92 Croisy-Delcey M.
Bisagni E.
J. Chem. Soc., Chem. Commun.
1984,
897
93 Rebstock AS.
Mongin F.
Trecourt F.
Queguiner G.
Org. Biomol. Chem.
2004,
2:
291
94 Epstajn J.
Jozwiak A.
Krysiak JK.
Lucka D.
Tetrahedron
1996,
52:
11025
95 Krapcho AP.
Waterhouse DJ.
Heterocycles
1999,
51:
7737
96 Kobayashi K.
Takanohashi A.
Watanabe S.
Morikawa O.
Konishi H.
Tetrahedron Lett.
2000,
41:
7657
97 Pardo M.
Joos K.
Schäfer W.
Liebigs Ann. Chem.
1979,
503
98 Kesteleyn B.
De Kimpe N.
J. Org. Chem.
2000,
65:
640
99 Kesteleyn B.
Nguyen Van T.
De Kimpe N.
Tetrahedron
1999,
55:
2091
100 Nguyen Van T.
Verniest G.
Claessens S.
De Kimpe N.
Tetrahedron
2005,
61:
2295
101 Adjanohoun EJ.
Ahyi AMR.
Dan Dicko L.
Daouda H.
Delmas M.
De Souza S.
Garba M.
Guinko S.
Kayonga A.
N’Golo D.
Raynal JL.
Saandou M.
Contribution aux Études Ethnobotaniques et Floristiques au Niger
ACCT;
France:
1985.
102 Harouna H.
Faure R.
Elias R.
Debrauwer L.
Saadou M.
Balansard G.
Boudon G.
Phytochemistry
1995,
39:
1483
103 Brown RT.
Scheimann F.
Stachulski AV.
J. Chem. Res., Synop.
1997,
370
104 Redoules D.
Perie J.
Tetrahedron Lett.
1999,
40:
4811
105 Nguyen Van T.
Claessens S.
Habonimana P.
Tehrani KA.
Van Puyvelde L.
Synlett
2006,
2469
106 Kesteleyn B.
Van Puyvelde L.
De Kimpe N.
J. Org. Chem.
1999,
64:
438
107 Lin P.
Jiang J.
Tetrahedron
2000,
56:
3635
108 Banks RE.
Smart BE.
Tatlow JC.
Organofluorine Chemistry, Principles and Commercial Application
Plenum;
New York:
1994.
109 Yang JJ.
Kirchmeier RL.
Shreeve JM.
J. Org. Chem.
1998,
63:
2600
110 McClinton MA.
McClinton DA.
Tetrahedron
1992,
48:
6555
111 Zang X.
Qing FL.
Yang Y.
Yu J.
Fu XK.
Tetrahedron Lett.
2000,
41:
2953
112 Hünig S.
Bau R.
Kemmer M.
Meixner H.
Metzenthin T.
Peters K.
Sinzger K.
Gulbis J.
Eur. J. Org. Chem.
1998,
335
113 Blazejewski JC.
Dorme R.
Wakselman C.
J. Chem. Soc., Perkin Trans. 1
1997,
1861
114 Nguyen Van T.
Kesteleyn B.
De Kimpe N.
Tetrahedron
2002,
1:
121
115 Rouhi AM.
Chem. Eng. News
2003,
(13):
77
116 Newman DJ.
Cragg GM.
Snader KM.
J. Nat. Prod.
2003,
66:
1022
