The first stereospecific approach to both enantiomers of mellein

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2153-2158

  Dimitriadis, Christian ^a   Gill, Melvyn ^a   Harte, Michael F ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCOUMARIN DERIVATIVE; MELLEIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIMETRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030862813     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00217-6     Document Type: Article

References (16)

1. Hill, R. A. Prog. Chem. Org. Nat. Prods. 1986, 49, 1-78.
2. For an alternative system of nomenclature, see Cornforth, J. W. Aust. J. Chem. 1993, 46, 157-170.
3. Nishikawa, H. J. Agric. Chem. Soc. Jpn. 1933, 9, 772-774. Yabuta, T.; Sumiki, Y. J. Agric. Chem. Soc. Jpn. 1933, 9, 1264-1275.
4. Nishikawa, H. J. Agric. Chem. Soc. Jpn. 1933, 9, 772-774. Yabuta, T.; Sumiki, Y. J. Agric. Chem. Soc. Jpn. 1933, 9, 1264-1275.
5. Mori, K.; Gupta, A. K. Tetrahedron 1985, 41, 5295-5299.
6. Both enantiomers of propylene oxide are available commercially, however, for cost efficiency, we prepare the (S)-enantiomer ent-3 from ethyl (S)-lactate: Golding, B. T.; Hall, D. R.; Sakrika, S. J. Chem. Soc., Perkin Trans. 1 1973, 1214-1220.
7. Gill, M. in "The Chemistry of Natural Products", 2nd Edition, R. H. Thomson (Ed.), Blackie A & P, 1993, pp 60-105.
8. Poch, G. K.; Gloer, J. B. J. Nat. Prod. 1989, 52, 257-260.
9. Cotterill, A. S.; Gill, M.; Milanovic, N. M. J. Chem. Soc., Perkin Trans. I 1995, 1215-1223.
10. Harland, P. A.; Hodge, P. Synthesis 1982, 223-225. Arai, Y.; Kamikawa, T.; Kubota, T. Bull. Chem. Soc. Jpn. 1973, 46, 3311-3312.
11. Harland, P. A.; Hodge, P. Synthesis 1982, 223-225. Arai, Y.; Kamikawa, T.; Kubota, T. Bull. Chem. Soc. Jpn. 1973, 46, 3311-3312.
12. Devys, M.; Bousquet, J. F.; Kollmann, A.; Barbier, M. Photochemistry 1980, 19, 2221-2222.
13. Blair, J.; Newbold, G. T. J. Chem. Soc. 1955, 2871-2875.
14. Schulz, B.; Sucker, J.; Aust, H. J.; Krohn, K.; Ludewig, K.; Jones, P. G.; Döring, D. Mycol. Res. 1995, 99, 1007-1015.
15. Grove, J. F.; Pople, M. J. Chem. Soc., Perkin Trans. 1 1979, 2048-2051.
16. Patterson, E. J.; Andres, W. W.; Bohonos, N. Experientia 1966, 22, 209-210.