Facile synthesis of 2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b- carboxylic acid methyl ester via a 9-BBN-mediated tertiary lactam reduction

Synthetic Communications

Volumn 38, Issue 21, 2008, Pages 3816-3822

  Fokas, Demosthenes ^a,b   Wang, Zhimin ^a  

^a ARQULE INC   (United States)

^b UNIVERSITY OF IOANNINA   (Greece)

Author keywords

9 BBN; Dimethyl ketoglutarate; Lactam reduction; Tryptamine

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; GLUTARIC ACID DERIVATIVE; INDOLE ALKALOID; INDOLE DERIVATIVE; LACTAM; NONANE; TERTIARY AMINE; TRYPTAMINE;

ARTICLE; POLYMERIZATION; REDUCTION; SYNTHESIS;

EID: 54049094757     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802238684     Document Type: Article

References (26)

1. For a review of the indole alkaloids, see (a) Kam, T.-S.; Choo, Y.-M. In Alkaloids: Chemistry and Biology; G. A. Cordell (Ed.); Academic Press: New York, 2006; vol. 63, pp. 181-337;
2. (b) Hesse, M. In Alkaloids: Nature's Curse or Blessing; Wiley-VCH: Weinheim, 2002; p. 414;
3. (c) Fattorusso, E.; Taglialatela-Scafati, O. In Modern Alkaloids; Wiley-VCH: Weinheim, 2007; p. 665.
4. Fokas, D.; Yu, L.; Baldino, C. M. Strategies for the synthesis of novel indole alkaloid-based screening libraries for drug discovery. Mol. Div. 2005, 9, 81-89.
5. Houlihan, W. J.; Manning, R. E. Azecino- and azonino[5,4-b] indoles. U.S. Patent 3,478,051, 1969;
6. (b) Herbst, D. R.; Smith, H. Indole fused heterocyclic diuretic compounds. U.S. Patent 3,943,148, 1976;
7. (c) Herbst, D.; Rees, R.; Hughes, G. A.; Smith, H. The preparation and biological activities of some azonino- and azecinoindoles and benzazecines. J. Med. Chem. 1966, 9, 864-868;
8. (d) Takahashi, T.; Inoue, H.; Horigome, M.; Momose, K.; Sugita, M.; Katsuyama, K.; Suzuki, C.; Nagai, S.; Nagase, M.; Nakamaru, K. Indole derivatives and anti-ulcer compositions. Eur. Pat. 535529, 1997.
9. (a) Corsano, S.; Algieri, S. Indole alkaloids, III. Ann. Chim. 1960, 50, 75-82;
10. (b) Meyers, A. I.; Loewe, M. F. The N-9, C-1 dianion of tetrahydro-β-carbolines: Regioselective alkylation leading to indole alkaloid systems. Tetrahedron Lett. 1984, 25, 2641-2644;
11. (c) Ashcroft, W. R.; Martinez, S. J.; Joule, J. A. Relative stabilities of 5-membered cyclic allylamine/enamine systems. Tetrahedron 1981, 37, 3005-3007;
12. (d) Mandal, S. B.; Giri, V. S.; Sabeena, M. S.; Pakrashi, S. C. Reduction of lactams and thiolactams by sodium borohydride: Application in the synthesis of some alkaloids. J. Org. Chem. 1988, 53, 4236-4241;
13. (e) Bernotas, R. C.; Cube, R. V. The use of triphenylphosphine-diethyl azodicarboxylate (DEAD) for the cyclization of 1,4- and 1,5-amino alcohols. Tetrahedron Lett. 1991, 32, 161-164;
14. (f) Knoelker, H.-J.; Agarwal, S. Novel three-step synthesis of (±)-harmicine. Synlett 2004, 1767-1768;
15. 5 selective antagonist. J. Med. Chem. 2006, 49, 760-769.
16. (a) Itoh, T.; Miyazaki, M.; Nagata, K.; Nakamura, S.; Ohsawa, A. Syntheses of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and harmicine using a chiral 1-allyl-1,2,3,4-tetrahydro-β-carboline as the starting material. Heterocycles 2004, 63, 655-661;
17. (b) Szawkalo, J.; Czarnocki, S. J.; Zawadzka, A.; Wojtasiewicz, K.; Leniewski, A.; Maurin, J. K.; Czarnocki, Z.; Drabowicz, J. Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Tetrahedron: Asymmetry 2007, 18, 406-413;
18. (c) Allin, S. M.; Gaskell, S. N.; Elsegood, M. R. J.; Martin, W. P. A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7-b]indole alkaloid (+)-harmicine. Tetrahedron Lett. 2007, 48, 5669-5671.
19. Magnus, P.; Ladlow, M.; Kim, C. S.; Boniface, P. Use of the Barton decarboxylation procedure in indole alkaloid chemistry. Heterocycles 1989, 28, 951-956.
20. Magnus, P.; Ladlow, M.; Elliott, J.; Kim, C. S. Nonoxidative methodology for the synthesis of vinblastine and vincristine models. J. Chem. Soc., Chem. Commun. 1989, 8, 518-520.
21. Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N. Synthesis of strychnine via the Wieland-Gumlich aldehyde. J. Am. Chem. Soc. 1993, 115, 8116-8129.
22. Cava, M. P.; Levinson, M. I. Thionation reactions of Lawesson's reagents. Tetrahedron 1985, 41, 5061-5087.
23. Back, T. G.; Baron, D. L.; Yang, K. Desulfurization with nickel and cobalt boride: Scope, selectivity, stereochemistry, and deuterium-labeling studies. J. Org. Chem. 1993, 58, 2407-2413.
24. Magnus, P.; Gazzard, L.; Hobson, L.; Payne, A. H.; Rainey, T. J.; Westlund, N.; Lynch, V. Synthesis of the Kopsia alkaloids (±)- pauciflorine B, (±)-lahadinine B, (±)-kopsidasine, (±)-kopsidasine-N-oxide, (±)-kopsijasminilam and (±)-11-methoxykopsilongine. Tetrahedron 2002, 58, 3423-3443.
25. (a) Collins, C. J.; Lanz, M.; Singaram, B. Facile reduction of tertiary lactams to cyclic amines with 9-borabicyclo[3.3.1]nonane (9-BBN). Tetrahedron Lett. 1999, 40, 3673-3676;
26. (b) Godjoian, G.; Singaram, B. Controlled reduction of tertiary amides to the corresponding aldehydes or amines using dialkylboranes. Tetrahedron Lett. 1997, 38, 1717-1720.