Thiol-oxygen cooxidation of monoterpenes. Synthesis of endoperoxides structurally related to antimalarial yingzhaosu A

Synlett

Volumn , Issue 2, 1998, Pages 122-124

  Bachi, Mario D ^a   Korshin, Edward E ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000015486     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1587     Document Type: Article

References (20)

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6. Bachi, M. D.; Korshin, E. E.; Ploypradith, P.; Cumming, J. N.; Xie, S.; Shapiro, T. A.; Posner, G. H. 1997, in preparation.
7. Preliminary SAR results will be given in reference 6.
8. Oswald, A. A.; Wallace, T. J. In The Chemistry of Organic Sulfur Compounds; N. Kharasch and C. Y. Meyers, Ed.; Pergamon Press: Oxford, 1966; Vol. 2; pp 205.
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12. Beckwith, A. L. J.; Wagner, R. D. J. Org. Chem. 1981, 46, 3638.
13. (a) Feldman, K. S.; Simpson, R. E. J. Am. Chem. Soc. 1986, 108, 1328.
14. (b) Feldman, K. S.; Simpson, R. E. J. Am. Chem. Soc. 1989, 111, 4878.
15. Feldman, K. S. Synlett 1995, 217.
16. S-(-)-Limonene (13) and (-)-carvone are commercially available, derivatives 14-16 were obtained by standard methods from (-)-carvone.
17. Endoperoxides 17-24 are thermally stable at rt for at least 6 months and in solutions of inert organic solvents at 60°C for at least 5 h.
18. Caution is to be taken in handling potentially explosive di-tertbutyl peroxalate and mixtures of organic solvents and oxygen.
19. 13C HMQC). All sulfones (21a,b-24a) were additionally characterized by elemental microanalysis or CI HRMS. The 3D-structure of endoperoxide 20a (crystallized as monohydrate) was determined by X-ray diffraction analysis. The 3D-structure of all other endoperoxides described in this paper was further corroborated by correlation of their NMR spectra with those of 20a monohydrate.
20. Selected NMR spectra: