Efficient route to medium-ring benzo- and azabenzo-lactones

Synthetic Communications

Volumn 38, Issue 6, 2008, Pages 889-904

  Metay, Estelle ^a   Léonel, Eric ^a   Nédélec, Jean Yves ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

Electrochemical arylation; Medium ring lactones; Nickel catalysis

Indexed keywords

ALDEHYDE; LACTONE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; ELECTROCHEMICAL ANALYSIS; SYNTHESIS;

EID: 39749186515     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701845415     Document Type: Article

References (15)

1. (a) Parenty, A.; Moreau, X.; Campagne, J.-M. Macrolactonizations in the total synthesis of natural products. Chem. Rev. 2006, 106, 911-939;
2. (b) Shiina, I. Total synthesis of natural 8- and 9-membered lactones: Recent Advancements in medium-sized ring formation. Chem. Rev. 2007, 107, 239-273;
3. (c) Bartra, M.; Urpi, F.; Vilarrasa, J. Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukas, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, pp. 1-65.
4. Rousseau, G. Medium ring lactones. Tetrahedron 1995, 51, 2777-2849.
5. (a) Ruzicka, L.; Stoll, M.; Schinz, H. Carbon rings. II. Synthesis of carbocyclic ketones of 10- to 18-membered rings. Helv. Chem. Acta. 1926, 9, 249-264;
6. (b) Ruzicka, L.; Brugger, W. Carbon rings. V. Preparation of a nine-membered from an eight-membered carbon ring. Helv. Chem. Acta. 1926, 9, 399-408;
7. (c) Ziegler, K.; Eberle, H.; Ohlinger, H. Polymembered ring system. I. Synthesis of polymethylene ketones with more than six-membered rings. Liebigs Ann. Chem. 1933, 504, 126-128.
8. (a) Métay, E.; Léonel, E.; Sulpice-Gaillet, C.; Nédélec, J.-Y. Synthesis of precursors for medium-ring aromatic lactones. Synthesis 2005, 1682-1688;
9. (b) Métay, E.; Léonel, E.; Condon, S.; Nédé lec, J.-Y. Acces to a new family of medium ring aromatic lactones. Tetrahedron 2006, 62, 8515-8524.
10. Gibson, S. E.; Guillo, N.; Middelton, R. J.; Thuilliez, A.; Tozer, M. J. Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations. J. Chem. Soc., Perkin Trans. 1 1997, 447-455.
11. Narisada, M.; Horibe, I.; Watanabe, F.; Takeda, K. Selective reduction of aryl halides and α,β-unsaturated esters with sodium borohydride-cuprous chloride in methanol and its application to deuterium labeling. J. Org. Chem. 1989, 54, 5308-5313.
12. Ishihara, K.; Kubota, M.; Kurihara, H. Yamamoto H. Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides. J. Org. Chem. 1996, 61, 4560-4567.
13. Bonnet, V.; Mongin, F.; Trécourt, F.; Quéguiner, G.; Knochel, P. Syntheses of substituted pyridines, quinolines and diazines via palladium-catalysed cross-coupling of aryl Grignard reagents. Tetrahedron 2002, 58, 4429-4438.
14. Read, M. W.; Ray, P. S. Synthesis of a 1,8-naphthyridin-5-one derivative via an intraamolecular 1,3-dipolar cycloaddition reaction. J. Heterocyclic Chem. 1995, 32, 1595-1597.
15. Kato, Y.; Niiyama, K.; Jona, H.; Okada, S.; Akao, A.; Hiraga, S.; Tsuchiya, Y.; Tomimoto, K.; Mase, T. Asymmetric synthesis of a selective endothelin A receptor antagonist. Chem. Pharm. Bull. 2002, 50, 1066-1072.