Selective protection of the C(7) and C(10) hydroxyl groups in 10- deacetyl baccatin III

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 2883-2886

  Holton, Robert A ^a   Zhang, Zhuming ^a   Clarke, Paul A ^a   Nadizadeh, Hossain ^a   Procter, D John ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Acylation; Lanthanides; Protecting groups; Taxoid

Indexed keywords

10 DEACETYLBACCATIN III; BACCATIN III; HYDROXYL GROUP; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032492929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00424-9     Document Type: Article

References (20)

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15. 6. Greene, et. al., report that they were unable to achieve this transformation (ref. 5).
16. 7. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed., John Wiley & Sons, Inc.: 1991, New York.
17. 8. Reagents 10, 11, and 12 were prepared via a slight modification of the reported procedure: Mawhinney, T. P.; Madson, M. A. J. Org. Chem. 1982, 47, 3336.
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19. 10. Greene, et. al. (ref 5) reported a yield of 85% for this transformation.
20. 11. The preparation of 7-troc baccatin III has been reported by Magri, N. F.; Kingston, D. G. I.; Jitrangsri, C.; Piccariello, T. J. Org. Chem. 1986, 51, 3239; Also reported by Potier, et. al. (ref 4b), although no yield was given.