This review covers the synthesis of various cyclic peptide natural products possessing highly functionalized tryptophan residues, focusing on the examples of diazonamide A, the TMC-95 compounds, the celogentin/moroidin family and the complestatin/chloropeptin system. Recent efforts toward the preparation of these modified-tryptophan-containing peptides will be outlined, focusing primarily on the novel methods for the assembly of the highly functionalized indole/tryptophan moieties at the core of these structures.
LindquistN, FenicalW, Van DuyneGD, ClardyJ. (1991) Isolation and structure determination of diazonamides A and B, unusual cytotoxic metabolites from the marine ascidian Diazona chinesis. Journal of the American Chemical Society, 113, 2303–2304.
2.
Cruz-MonserrateZ, VervoortHC, BaiR, NewmanDJ, HowellSB, LosG, MullaneyJT, WilliamsMD, PettitGR, FenicalW, HamelE. (2003) Diazonamide A and a synthetic structural analog: disruptive effects on mitosis and cellular microtubules and analysis of their interactions with tubulin. Molecular Pharmacology, 63, 1273–1280.
3.
LiJ, JeongS, EsserL, HarranPG. (2001) Total synthesis of nominal diazonamides–part 1: convergent preparation of the structure proposed for (–)-diazonamide A. Angewandte Chemie International Edition, 40, 4765–4770.
4.
HarranPG. (2001) Total synthesis of nominal diazonamides–part 2: on the true structure and origin of natural isolates. Angewandte Chemie International Edition, 40, 4770–4773.
5.
BurgettAWG, LiQ, WeiQ, HarranPG. (2003) A concise and flexible total synthesis of (–)-diazonamide A. Angewandte Chemie International Edition, 42, 4961–4966.
6.
(a) NicolaouKC, BellaM, ChenDYK, HuangX, LingT, SnyderSA. (2002) Total synthesis of diazonamide A. Angewandte Chemie International Edition, 41, 3495–3499;
7.
NicolaouKC, ChenDYK, HuangX, LingT, BellaM, SnyderSA. (2004) Chemistry and biology of diazonamide A: first total synthesis and confirmation of the true structure. Journal of the American Chemical Society, 126, 12888–12896.
8.
NicolaouKC, RaoPB, HaoJ, ReddyMV, RassiasG, HuangX, ChenDYK, SnyderSA. (2003) The second total synthesis of diazonamide A. Angewandte Chemie International Edition, 42, 1753–1758;
9.
NicolaouKC, HaoJ, ReddyMV, RaoPB, RassiasG, SnyderSA, HuangX, ChenDYK, BrenzovichWE, GiusepponeN, GiannakakouP, O'BrateA. (2004) Chemistry and biology of diazonamide A: second total synthesis and biological investigations. Journal of the American Chemical Society, 126, 12897–12906.
10.
(a) SperryJ, MoodyCJ. (2006) Biomimetic approaches to diazonamide A. Direct synthesis of the indole bis-oxazole fragment by oxidation of a TyrValTrpTrp tetrapeptide. Chemical Communications, 2397–2399;
11.
DaviesJR, KanePD, MoodyCJ. (2005) The diazo route to diazonamide A. Studies on the indole bis-oxazole fragment. Journal of Organic Chemistry, 70, 7305–7316.
12.
KohnoJ, KoguchiY, NishioM, NakaoK, KurodaM, ShimizuR, OhnukiT, KomatsubaraS. (2000) Structures of TMC-95A–D: novel proteasome inhibitors from Apiospora montagnei Sacc. TC 1093. Journal of Organic Chemistry, 65, 990–995.
13.
MaD, WuQ. (2000) Enantioselective construction of the oxidized tryptophan fragment of proteasome inhibitors TMC-95A and TMC-95B. Tetrahedron Letters, 41, 9089–9093.
14.
MaD, WuQ. (2001) Synthesis of the biaryl moiety of the proteasome inhibitors TMC-95 via a ligandless Pd(OAc)2-catalyzed Suzuki-coupling reaction. Tetrahedron Letters, 42, 5279–5281.
15.
LinS, DanishefskySJ. (2001) Synthesis of the functionalized macrocyclic core of proteasome inhibitors TMC-95A and B. Angewandte Chemie International Edition, 40, 1967–1970.
16.
(a) LinS, DanishefskySJ. (2002) Angewandte Chemie International Edition, 41, 512–515;
17.
LinS, YangZQ, KwokBHB, KoldobskiyM, CrewsCM, DanishefskySJ. (2004) Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR. Journal of the American Chemical Society, 126, 6347–6355.
18.
(a) InoueM, FuruyamaH, SakazakiH, FuruyamaH, HiramaM. (2001) Stereocontrolled synthesis of the northern part of potent proteasome inhibitor TMC-95A. Organic Letters, 3, 2863–2865;
19.
InoueM, SakazakiH, FuruyamaH, HiramaM. (2003) Total synthesis of TMC-95A. Angewandte Chemie International Edition, 42, 2654–2657.
20.
AlbrechtBK, WilliamsRM. (2004) A concise, total synthesis of the TMC-95A/B proteasome inhibitors. Proceedings of the National Academy of Sciences, USA, 101, 11949–11954.
21.
(a) AlbrechtBK, WilliamsRM. (2003) A concise, formal total synthesis of the TMC-95A/B proteasome inhibitors. Organic Letters, 5, 197–200.
22.
AlbrechtBK, WilliamsRM. (2001) Entry into the bi-aryl moiety of the TMC-95 proteasome inhibitors via the Stille protocol. Tetrahedron Letters, 42, 2755–2757.
23.
(a) KanekoI, KamoshidaK, TakahashiS. (1989) Complestatin, a potent anti-complement substance produced by Streptomyces lavendulae. I. Fermentation, isolation and biological characterization. Journal of Antibiotics, 42, 236–241;
24.
SetoH, FujiokaT, FurihataK, KanekoI, TakahashiS. (1989) Structure of complestatin, a very strong inhibitor of protease activity of complement in the human complement system. Tetrahedron Letters, 30, 4987–4990.
25.
(a) MatsuzakiK, OginoT, SunazukaT, TanakaH, OmuraS. (1997) Chloropeptins, new anti-HIV antibiotics inhibiting gp120-CD4 binding from Streptomyces sp. II. Structure elucidation of chloropeptin I. Journal of Antibiotics, 50, 66–69;
26.
MatsuzakiK, IkedaH, OginoT, MatsumotoA, WoodruffHB, TanakaH, OmuraS. (1994) Chloropeptins I and II, novel inhibitors against gp120-CD4 binding from Streptomyces sp. Journal of Antibiotics, 47, 1173–1174.
27.
SinghSB, JayasuriyaH, SalituroGM, ZinkDL, ShafieeA, HeimbuchB, SilvermanKC, LinghamRB, GenilloudO, TeranA, VilellaD, FelockP, HazudaD. (2001) The complestatins as HIV-1 integrase inhibitors. Efficient isolation, structure elucidation, and inhibitory activities of isocomplestatin, chloropeptin I, new complestatins, A and B, and acid-hydrolysis products of chloropeptin I. Journal of Natural Products, 64, 874–882.
28.
JayasuriyaH, SalituroGM, SmithSK, HeckJV, GouldSJ, SinghSB, HomnickCF, HollowayMK, PitzenbergerSM, PataneMA. (1998) Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin. Tetrahedron Letters, 39, 2247–2248.
29.
(a) GurjarMK, TripathyNK. (1997) Synthesis of C-C biaryl segment of complestatin and chloropeptin: approach to the right hand CEF-ring system of complestatin. Tetrahedron Letters, 38, 2163–2166;
30.
CarbonnelleAC, ZamoraEG, BeugelmansR, RoussiG. (1998) The first synthesis of simplfied 16- and 17-membered ring macropolypeptides containing the phenyl-indole system of kistamycin and chloropeptin I, II. Tetrahedron Letters, 39, 4471–4472;
31.
YamadaY, AkibaA, ArimaS, OkadaC, YoshidaK, ItouF, KaiT, SatouT, TakedaK, HarigayaY. (2005) Synthesis of linear tripeptides for right-hand segments of complestatin. Chemical and Pharmaceutical Bulletin, 53, 1277–1290.
32.
ElderAM, RichDH. (1999) Two syntheses of the 16- and 17-membered DEF ring systems of chloropeptin and complestatin. Organic Letters, 1, 1443–1446.
33.
DengH, JungJK, LiuT, KuntzKW, SnapperML, HoveydaAH. (2003) Total synthesis of anti-HIV agent chloropeptin I. Journal of the American Chemical Society, 125, 9032–9034.
34.
ShinoharaT, DengH, SnapperML, HoveydaAH. (2005) Isocomplestatin: total synthesis and stereochemical revision. Journal of the American Chemical Society, 127, 7334–7336.
35.
(a) LeungCTW, WilliamsDH, BarnaJCJ, FotiS, OerlichsPB. (1986) Structural studies on the peptide moroidin from Laportea moroides. Tetrahedron, 42, 3333–3348.
36.
KahnSD, BoothPM, WalthoJP, WilliamsDH. (1989) Computer-assisted structure determination. Structure of the peptide moroidin from Laportea moroides. Journal of Organic Chemistry, 54, 1901–1904.
37.
(a) KobayashiJ, SuzukiH, ShimboK, TakeyaK, MoritaH. (2001) Celogentins A–C, new antimitotic bicyclic peptides from the seeds of Celosia argentea. Journal of Organic Chemistry, 66, 6626–6633.
38.
SuzukiH, MoritaH, IwasakiS, KobayashiJ. (2003) New antimitotic bicyclic peptides, celogentins D–H, and J, from the seeds of Celosia argentea. Tetrahedron, 59, 5307–5315.
39.
SuzukiH, MoritaH, ShiroM, KobayashiJ. (2004) Celogentin K, a new cyclic peptide from the seeds of Celosia argentea and X-ray structure of moroidin. Tetrahedron, 60, 2489–2495.
40.
MoritaH, ShimboK, ShigemoriH, KobayashiJ. (2000) Antimitotic activity of moroidin, a bicyclic peptide from the seeds of Celosia argentea. Bioorganic and Medicinal Chemistry Letters, 10, 469–471.
41.
ComberMF, MoodyCJ. (1992) 2-Chloro-1-methoxymethylindole-3-carboxaldehyde: introduction of nucleophiles into the indole 2-position and an approach to the unusual TrpHis fragment of moroidin. Synlett, 731–733.
42.
HarrisonJR, MoodyCJ. (2003) The Horner-Wadsworth-Emmons reaction in the synthesis of macrocyclic peptides: the Trp-His-Gly-Arg derived macrocycle of moroidin. Tetrahedron Letters, 44, 5189–5191.
43.
HeL, YangL, CastleSL. (2006) Synthesis of the celogentin C right-hand ring. Organic Letters, 8, 1165–1168.
44.
CastleSL, SrikanthGSC. (2003) Catalytic asymmetric synthesis of the central tryptophan residue of celogentin C. Organic Letters, 5, 3611–3614.
45.
MaC, LiuX, LiX, Flippen-AndersonJ, YuS, CookJM. (2001) Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction. Journal of Organic Chemistry, 66, 4525–4542.
46.
YuenAKL, JolliffeKA, HuttonCA. (2006) Preparation of the central tryptophan moiety of the celogentin/moroidin family of anti-mitotic cyclic peptides. Australian Journal of Chemistry, 59, submitted.
47.
(a) BentleyDJ, SlawinAMZ, MoodyCJ. (2006) Total synthesis of stephanotic acid methyl ester. Organic Letters, 8, 1975–1978;
48.
BentleyDJ, MoodyCJ. (2004) Asymmetric synthesis of the central tryptophan residue of stephanotic acid. Organic & Biomolecular Chemistry, 2, 3545–3547.
49.
YoshikawaK, TaoS, AriharaS. (2000) Stephanotic acid, a novel cyclic pentapeptide from the stem of Stephanotis floribunda. Journal of Natural Products, 63, 540–542.