Synthesis of an octahydroindolinone scaffold for a diversity-based chemical compound library

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5411-5413

  Keaney, Gregg F ^a   Johannes, Charles W ^a  

^a Infinity Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMARYLLIDACEAE ALKALOID; INDOLE DERIVATIVE; LACTAM DERIVATIVE; NATURAL PRODUCT; OCTAHYDROINDOLINONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

AMARYLLIDACEAE;

EID: 34347323943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.018     Document Type: Article

References (22)

1. Jin Z. Nat. Prod. Rep. 20 (2003) 606-614
2. Padwa A., Dimitroff M., Waterson A.G., and Wu T. J. Org. Chem. 62 (1997) 4088-4096
3. Padwa A., Brodney M., Dimitroff M., Liu B., and Wu T. J. Org. Chem. 66 (2001) 3119-3128
4. Padwa A., Lee H.I., Rashatasakhon P., and Rose M. J. Org. Chem. 69 (2004) 8209-8218
5. Padwa A., Rashatasakhon P., Ozdemir A.D., and Willis J. J. Org. Chem. 70 (2005) 519-528
6. Padwa A., and Wang Q. Org. Lett. 6 (2004) 2189-2192
7. Padwa A., and Wang Q. J. Org. Chem. 71 (2006) 7391-7402
8. Padwa A., and Wang Q. J. Org. Chem. 71 (2006) 3210-3220
9. Lautens M., Dockendorff C., Fagnou K., and Malicki A. Org. Lett. 4 (2002) 1311-1314
10. Lautens M., Fagnou K., and Yang D. J. Am. Chem. Soc. 125 (2003) 14884-14892
11. Acetonide formation (4→5) using these conditions was reported concurrently by Padwa et al. (Ref. 7).
12. This reaction may proceed through an epoxide intermediate; see:. Vyvyan J.R., Meyer J.A., and Meyer K.D. J. Org. Chem. 68 (2003) 9144-9147
13. A recent publication, which describes reduction attempts on a related hexahydroindolinone system, demonstrates that the steric bulk of the substituent at the ring junction affects the stereochemical outcome of the reduction: see:. Brodney M.A., Cole M.L., Freemont J.A., Kyi S., Junk P.C., Padwa A., Riches A.G., and Ryan J.H. Tetrahedron Lett. 48 (2007) 1939-1943
14. Martinelli M.J., Vaidyanathan R., Pawlak J.M., Nayyar N.K., Dhokte U.P., Koecke C.W., Zollars L.M.H., Hoher E.D., Khau V.V., and Kosmrlj B. J. Am. Chem. Soc. 124 (2002) 3578-3585
15. David S., and Hanessian S. Tetrahedron 41 (1985) 643-663
16. Interestingly, nosylation did not proceed without dibutyltin oxide in the reaction mixture.
17. Stafford J.A., Brackeen M.F., Karanewsky D.S., and Valvano N.L. Tetrahedron Lett. 34 (1993) 7873-7876
18. 9S): C, 45.46; H, 4.56; N, 6.51; S, 7.01.
19. 2 = 0.1062. Crystallographic data for 10 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 647518. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
20. Fukuyama T., Jow C.-K., and Cheung M. Tetrahedron Lett. 36 (1995) 6373-6374
21. Maligres P.E., See M.M., Askin D., and Reider P.J. Tetrahedron Lett. 38 (1997) 5253-5256
22. Mitchell J.M., and Shaw J.T. Angew. Chem., Int. Ed. 45 (2006) 1722-1726