Chemoenzymatic synthesis of the morphine skeleton via radical cyclization and a C10-C11 closure

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8155-8158

  Butora, Gabor ^a   Hudlicky, Tomas ^a   Fearnley, Stephen P ^a   Gum, Andrew G ^a   Stabile, Michele R ^a   Abboud, Khalil ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MORPHINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030569320     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01867-9     Document Type: Article

References (28)

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17. 3. The following sequence was carried out in our laboratories in the natural enantiomer series (ca. 10 % yield): (equation presented)
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20. 6. In E. coli JM109 (pDTG 602) the catechol dehydrogenase is still synthesized but the expression of enzymes for the next step in the degradation, namely the ortho-scission, has been blocked. See: Zylstra, G. J.; Gibson, D. T. J. Biol. Chem. 1989, 164, 14940.
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22. 2NEt), was coupled with oxazolone to yield 10.
23. 9. Full x-ray crystallography data will be published in Acta Cryst. by Khalil Abboud, University of Florida.
24. 11 bonds are disconnected. For recent reference see: Cheng, C.-Y., Hsin, L.-W., Liou, J.-P. Tetrahedron, 1996, 52, 10935.
25. 11 closure is possible with compound containing the complete benzofuran unit.
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27. 13. All analytical and spectral data obtained were consistent with the structural assignments.
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