Synthesis of 3-amino-2,2-dimethyl-8-thia-1-azaspiro[4.5]decane

Synthetic Communications

Volumn 40, Issue 17, 2010, Pages 2571-2577

  Mai, Wenpeng ^a   Green, Sarah A ^a   Bates, Dallas K ^a   Fang, Shiyue ^a  

^a MICHIGAN TECHNOLOGICAL UNIVERSITY   (United States)

Author keywords

Grignard reactions; heterocycle; iodoaminocyclization; prenylation; spiro compound

Indexed keywords

3 AMINO 2,2 DIMETHYL 8 THIA 1 AZASPIRO[4.5]DECANE; AMINE; BENZYL DERIVATIVE; DECANE; HETEROCYCLIC COMPOUND; IMINE; IODINE; MAGNESIUM DERIVATIVE; PRENYLAMINE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 77955459116     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903289255     Document Type: Article

References (17)

1. Dake, G. Recent approaches to the construction of 1-azaspiro[4.5]decanes and related 1-azaspirocycles. Tetrahedron 2006, 62, 3467.
2. Sun, M.; Lu, H.; Wang, Y.; Yang, H.; Liu, H. Highly efficient formal synthesis of cephalotaxine, using the Stevens rearrangement-acid lactonization sequence as a key transformation. J. Org. Chem. 2009, 74, 2213.
3. Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Total synthesis of (±)-cocculolidine. Tetrahedron Lett. 2001, 42, 8003.
4. Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.; Faucette, L.; Johnson, R. K.; Faulkner, D. J. Fasicularin, a novel tricyclic alkaloid from the ascidian Nephteis fasicularis with selective activity against a DNA repair-deficient organism. Tetrahedron Lett. 1997, 38, 363.
5. Arimoto, H.; Asano, S.; Uemura, D. Synthesis of pinnaic acid: Asymmetric construction of spirocyclic core. Tetrahedron Lett. 1999, 40, 3583.
6. Kan, T.; Fujimoto, T.; Ieda, S.; Asoh, Y.; Kitaoka, H.; Fukuyama, T. Stereocontrolled total synthesis of potent immunosuppressant FR901483. Org. Lett. 2004, 6, 2729.
7. Abe, H.; Aoyagi, S.; Kibayashi, C. Total synthesis of the tricyclic marine alkaloids (-)-lepadiformine, (+)-cylindricine C, and (-)-fasicularin via a common intermediate formed by formic acid-induced intramolecular conjugate azaspirocyclization. J. Am. Chem. Soc. 2005, 127, 1473.
8. Hurley, T. B.; Peukert, S.; Wattanasin, S. Preparation of purrolecarboxamides and pyridinecarboxamides as inhibitors of undecaprenyl pyrophosphate synthase. PCT Int. Appl. WO 2008014311, 2008.
9. Fischer, R.; Bretschneider, T.; Krueger, B.-W.; Santel, H. J.; Dollinger, M.; Erdelen, C.; Wachendorff-Neumann, U. Preparation of spirocyclic 1H-3-arylpyrrolidin-2,4-diones as pesticides. Ger. Offen. DE 4415334, 1995.
10. Diaba, F.; Puigbo, G.; Bonjoch, J. Synthesis of enantiopure 1-azaspiro[4.5]decanes by iodoaminocyclization of allylaminocyclohexanes. Eur. J. Org. Chem. 2007, 3038.
11. Rule, N. G.; Detty, M. R.; Kaeding, J. E.; Sinicropi, J. A. Syntheses of 4H-thiopyran-4-one 1,1-dioxides as precursors to sulfone-containing analogs of tetracyanoquinodi-methane. J. Org. Chem. 1995, 60, 1665.
12. Mazerolles, P.; Boussaguet, P.; Huc, V. 6-Chloro-1-hexene and 8-chloro-1-octene; Org. Synth.; John Wiley & Sons: London, 1999; vol.76, p. 221.
13. Schkeryantz, J. M.; Woo, J. C. G.; Siliphaivanh, P.; Depew, K. M.; Danishefsky, S. J. Total synthesis of gypsetin, deoxybrevianamide E, brevianamide E, and tryprostatin B: Novel constructions of 2,3-disubstituted indoles. J. Am. Chem. Soc. 1999, 121, 11964.
14. Diaba, F.; Ricou, E.; Bonjoch, J. New insights into NIS-promoted aminocyclization: Synthesis of decahydroquinolines from 2-allylcyclohexylamines. Org. Lett. 2007, 9, 2633.
15. Bull, S. D.; Davies, S. G.; Fenton, G.; Mulvaney, A. W.; Prasad, R. S.; Smith, A. D. Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate. J. Chem. Soc., Perkin. Trans. 1 2000, 3765.
16. Knapp, S.; Levorse, A. T. Synthesis and reactions of iodo lactams. J. Org. Chem. 1988, 53, 4006.
17. Choi, Y.; George, C.; Strazewski, P.; Marquez, V. E. Synthesis of a conformationally locked version of puromycin amino nucleoside. Org. Lett. 2002, 4, 589.