Diverse alkanones by catalytic carbon insertion into the formyl C-H bond. Concise access to the natural precursor of achyrofuran

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3202-3205

  Wommack, Andrew J ^a   Moebius, David C ^a   Travis, Austin L ^a   Kingsbury, Jason S ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACHYROFURAN; ANTIDIABETIC AGENT; CARBON; FURAN DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; CHEMISTRY; DRUG DESIGN; NON INSULIN DEPENDENT DIABETES MELLITUS; SYNTHESIS;

CARBON; CATALYSIS; DIABETES MELLITUS, TYPE 2; DRUG DESIGN; FURANS; HYPOGLYCEMIC AGENTS; KETONES;

EID: 68149116124     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9010932     Document Type: Article

References (20)

1. 2 and aldehydes were Buchner and Curtius (1885), v. Pechman (1895), Meyer (1905), and Schlotterbeck (1907). For a review, see: Gutsche, C. D. Org. React. 1954, 8, 364-429.
2. For a modern example, see: Werner, R. M.; Shokek, O.; Davis, J. T. J. Org. Chem. 1997, 62, 8243-8246.
3. Loeschorn, C. A.; Nakajima, M.; McCloskey, P. J.; Anselme, J.-P. J. Org. Chem. 1983, 48, 4407-4410.
4. (a) Angle, S. R.; Neitzel, M. L. J. Org. Chem. 2000, 65, 64586461.
5. (b) Aggarwal, V. K.; de Vicente, J.; Pelotier, B.; Holmes, I. P.; Bonnert, R. V. Tetrahedron Lett. 2000, 41, 10327-10331.
6. Mahmood, S. J.; Saha, A. K.; Hossain, M. Tetrahedron 1998, 54, 349-358.
7. 2 and ethyldiazoacetate (respectively), see: (a) Aoyama, T.; Shioiri, T. Synthesis 1988, 228-229.
8. (b) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synlett 1994, 521-523.
9. (c) Maruoka, K.; Concepcion, A. B; Yamamoto, H. Synthesis 1994, 1283-1290.
10. (d) Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258-3260.
11. Aryldiazoacetates have been used to prepare a-quaternary aldehydes, but the chiral ketone is just a trace byproduct; see: (e) Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434-2435. See also:
12. (f) Dias, E. L.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 2001, 123, 2442-2443.
13. (g) Aggarwal, V. K.; Sheldon, C. G.; Macdonald, G. J.; Martin, W. P. J. Am. Chem. Soc. 2002, 124, 10300-10301.
14. (a) Moebius, D. C.; Kingsbury, J. S. J. Am. Chem. Soc. 2009, 131, 878-879.
15. (b) Our approach involves modification of two modern protocols for low-temperature hydrazone oxidation. See Supporting Information.
16. Xu, H.; Zhang, W.; Shu, D.; Werness, J. B.; Tang, W. Angew. Chem, Int. Ed. 2008, 47, 8933-8936.
17. 3 in toluene at -78 °C cleanly gives diphenylacetaldehyde upon warming. Epoxide rearrangement to aldehydes and ketones has been reported with the hydrates of erbium and cerium triflate: Procopio, A.; Dalpozzo, R.; De Nino, A.; Nardi, M.; Sindona, G.; Tagarelli, A. Synlett 2004, 2633-2635.
18. Carney, J. R.; Krenisky, J. M.; Williamson, R. T.; Luo, J. J. Nat. Prod. 2002, 65, 203-205.
19. For general commentary on new leads in the treatment of diabetes, see: Jarvis, L. M. Chem. Eng. News 2008, 86, 34-36.
20. Alternative means to formally achieve carbon insertion: Katritsky, A. R.; Toader, D.; Linghong, X. J. Org. Chem. 1996, 61, 7571-7577.