Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation/allylation-ring closing metathesis-oxidation sequence

Synlett

Volumn , Issue 10, 1999, Pages 1639-1641

  Carda, Miguel ^a   Castillo, Encarnación ^a   Rodríguez, Santiago ^a   Uriel, Santiago ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Allylic oxidation; Barbier allylation; Conjugated lactones; Ring closing metathesis

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE; FURAN DERIVATIVE; GAMMA LACTONE DERIVATIVE; KETONE; LACTONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032822799     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2897     Document Type: Article

References (22)

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4. For two recent reviews on olefin metathesis, see: (a) Armstrong, S.K. J. Chem.Soc.Perkin Trans. I, 1998, 371.
5. (b) Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413.
6. (c) Schrock, R. R. Tetrahedron 1999, 55, 8141.
7. (a) Ghosh, A.K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 4651.
8. (b) Bassindale, M.J.; Hamley, P.; Leitner, A.; Harrity, J.P.A. Tetrahedron Lett. 1999, 3247.
9. Carda, M.; Castillo, E.; Rodríguez, S.; Murga, J.; Marco, J.A. Tetrahedron: Asymmetry 1998, 9, 1117. Zinc worked well here and was preferred to indium because of its much lower price. These results are part of the Ph.D. Thesis of E.C. and will be published with detail in due course.
10. 4 = H) (unpublished result). (formula presented)
11. Fürstner, A.; Langemann, K. J.Am.Chem.Soc. 1997, 119, 9130.
12. 4 = H), which could not be obtained from the corresponding acrylate 7c but was easily prepared, however, via the allylation/RCM/oxidation sequence (Table 1): (formula presented)
13. (a) Delgado, M.; Martín, J.D. Tetrahedron Lett. 1997, 6299.
14. (b) Maier, M.E.; Bugl, M. Synlett 1998, 1390.
15. (a) Kirkland, T.A.; Grubbs, R.H. J.Org.Chem. 1997, 62, 7310.
16. (b) Chang, S.; Grubbs, R.H. J.Org.Chem. 1998, 63, 864. It is worth mentioning here that we have had good results working at a concentration of about 0.1M.
17. 4
18. Dauben, W.G.; Lorber, M.; Fullerton, D.S. J.Org.Chem. 1969, 34, 3857.
19. Salmond, W.G.; Barta, M.A.; Havens, J.L. J.Org.Chem. 1978, 43, 2057.
20. 2 (10 ml) and treated under Ar with 3 (25 mg, ca. 0.03 mmol). After stirring overnight at reflux, the reaction mixture was cone, in a rotary evaporator and chromatographed on silica gel (elution with hexane-EtOAc 9:1). B) With catalyst 4: 23 mg of the catalyst (ca. 0.03 mmol) was weighed in a dry box and placed in a flame-dried flask under argon. The substrate (0.5 mmol) was dissolved in dry, degassed benzene (5 ml) and added via syringe to the flask containing the catalyst. After stirring for 24 h at reflux, the reaction mixture was concentrated in a rotary evaporator and chromatographed on silica gel (elution with hexane-EtOAc 9:1).
21. 4, filtered, conc. in a rotary evaporator and chromatographed on silica gel (elution with hexane-EtOAc 9:1).
22. 3).