Efficient route to the pineal hormone melatonin by radical-based indole synthesis

Synthetic Communications

Volumn 33, Issue 20, 2003, Pages 3631-3641

  Thomson, Douglas W ^a   Commeureuc, Aurélien G J ^a   Berlin, Stefan ^a   Murphy, John A ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Indole; Melatonin; Radical; Synthesis

Indexed keywords

INDOLE DERIVATIVE; MELATONIN; N ETHYLPIPERIDINE HYPOPHOSPHITE; PINEAL BODY HORMONE; PIPERIDINE DERIVATIVE; RADICAL; SILANE DERIVATIVE; TRISTRIMETHYLSILYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG EFFECT; DRUG SYNTHESIS; HORMONE SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0141865651     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120024751     Document Type: Article

References (25)

1. Lerner, B.; Case, J.D.; Takahashi, Y.; Lee, T.H.; Mori, W. Structure of melatonin. J. Am. Chem. Soc. 1959, 80, 6084-6085.
2. (a) Zhdanova, I.V.; Wartman, R.J.; Regan, M.M.; Taylor, J.A.; Shi, J.P.; Leclair, O.U. Melatonin treatment for age-related insomnia. J. Clin. Endocr. Metab. 2001, 86, 4727-4730;
3. (b) Lynch, H.J.; Wurtman, R.J.; Moskowitz, M.A.; Archer, M.C.; Mo, M.H. Daily rhythm in human urinary melatonin. Science 1975, 187, 169-171.
4. (a) Reiter, R.J.; Acuna-Castroviejo, D.; Tan, D.X.; Burkhardt, S. Free radical-mediated molecular damage-mechanisms for the protective actions of melatonin in the central nervous system. Ann. N.Y. Acad. Sci. 2001, 939, 200-215;
5. (b) Barlow-Walden, L.R.; Reiter, R.J.; Abe, M.; Pablos, M.; Menendez-Pelaez, A.; Chen, L.-D.; and Poeggelar, B. Melatonin stimulates brain glutathione-peroxidase activity. Neurochem. Int. 1995, 26, 497-502;
6. (c) Reiter, R.J. Functional pleiotropy of the neurohormone melatonin-antioxidant protection and neuroendocrine regulation. Front. Neuroendocrinol 1995, 16, 383;
7. (d) Tan, D.X.; Poeggeler, B.; Reiter, R.J.; Chen, L.D.; Chen, S.; Manchester, L.C.; Barlow-Walden, L.R. The pineal hormone melatonin inhibits DNA-adduct formation induced by the chemical carcinogen safrole in vivo. Cancer Lett. 1993, 70, 65-71.
8. Poeggeler, B.; Miravalle, L.; Zagorski, M.G.; Wisniewski, T.; Chyan, Y.-J.; Zhang, Y.; Shao, H.; Bryant-Thomas, T.; Vidal, R.; Frangione, B.; Ghiso, J.; Pappolla, M.A. Melatonin reverses the profibrillogenic activity of apolipoprotein e4 on the alzheimer amyloid a beta peptide. Biochemistry 2001, 40, 14995-15001.
9. Jordan, A.; Hadfield, J.A.; Lawrence, N.J.; McGown, A.T. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med. Res. Rev. 1998, 18, 259-296; Banerjee, S.; Kerr, V.; Winston, M.; Kelleher, J.K.; Margulis, L. J. Protozool melatonin: inhibition of microtubule-based oral morphogenesis in Stento Coeruleus. 1972, 19, 108-113.
10. Jordan, A.; Hadfield, J.A.; Lawrence, N.J.; McGown, A.T. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med. Res. Rev. 1998, 18, 259-296; Banerjee, S.; Kerr, V.; Winston, M.; Kelleher, J.K.; Margulis, L. J. Protozool melatonin: inhibition of microtubule-based oral morphogenesis in Stento Coeruleus. 1972, 19, 108-113.
11. Nogales, E.; Wolf, S.G.; Downing, K.H. Structure of the alpha beta tubulin dimer by electron crystallography. Nature 1998, 391, 199-203.
12. Edmondson, S.; Danishefsky, S.J.; Sepp-Lorenzino, L.; Rosen, N. Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues. J. Am. Chem. Soc. 1999, 121, 2147-2155.
13. (a) Somei, M.; Fukui, Y.; Hasegawa, M.; Oshikiri, N.; Hayashi, T. Syntheses of melatonin and its derivatives. Heterocycles 2000, 53, 1725-1725;
14. (b) Hwang, K.J.; Lee, T.S. A practical synthesis of N-acetyl-5-methoxytryptamine (melatonin). Synth. Commun. 1999, 29, 2099-2104 and references therein.
15. (a) Quiclet-Sire, B.; Sortais, B.; Zard, S.Z. A convergent approach to 2-substituted-5-methoxyindoles application to the synthesis of Melatonin. Chem. Commun. 2002, 1692-1693 (and 1988).
16. (a) Murphy, J.A.; Scott, K.A.; Sinclair, R.S.; Lewis, N. A new synthesis of indoles. Tetrahedron Lett. 1997, 38, 7295-7298;
17. (b) Murphy, J.A.; Scott, K.A.; Sinclair, R.S.; Martin, C.G.; Kennedy, A.R.; Lewis, N. A radical based addition-elimination route for the preparation of indoles. J. Chem. Soc. Perkin Trans. 2000, 1, 2395-2408.
18. (a) Dittami, J.P.; Ramanathan, H. Intramolecular radical cyclization reactions-an approach to the indole alkaloids. Tetrahedron Lett. 1988, 29, 45-48;
19. 2-enhanced functional analogs of cc-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]-indol-4-one (CBI) left-hand subunit. J. Org. Chem. 1990, 55, 5823-5832;
20. 2 [(±)-(3bR*,4aS*)-, (+)-(3bR,4aS)- and (-)-(3bS,4aR)-Deoxy-CC-1065]. J. Amer. Chem. Soc. 1988, 110, 4796-4807;
21. 2-promoted aryl radical cyclization-a new synthetic entry into heterocycles. Tetrahedron Lett. 1991, 32, 1737-1740;
22. (e) Hodgson, D.M.; Wells, C. Chromium(II)-mediated nickel(ii)-catalyzed cyclizations of (iodoaryl)-substituted alkynes and alkynals. Tetrahedron Lett. 1994, 35, 1601-1604.
23. Lizos, D.E.; Murphy, J.A. Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclization of iodoaryl alkenyl azides. Org. Biomol. Chem. 2003, 1, 117-122.
24. Allan, R.D.; Johnston, G.A.R.; Twitchin, B. Synthesis of analogues of GABA. V. trans and cis isomers of some 4-amino-3-halogenobut-2-enoic Acids. Aust. J. Chem. 1980, 33, 1115-1122.
25. Revial, G.; Jabin, I.; Lim, S.; Pfau, M. Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin, melatonin, and bufotenin. J. Org. Chem. 2002, 67, 2252-2256.