Semisynthesis of D-ring-modified taxoids: Thietane derivatives from taxine B

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4891-4894

  Payré, Christophe ^a   Al Mourabit, Ali ^a   Mercklé, Ludovic ^a   Ahond, Alain ^a   Poupat, Christiane ^a   Potier, Pierre ^a  

^a CNRS   (France)

Author keywords

7 deoxothiabaccatin III; Protected taxicine I; Taxine B; Thietane

Indexed keywords

DOCETAXEL; PACLITAXEL; TAXINE B; TAXOID; THIETANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG ISOLATION; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0034686210     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00727-9     Document Type: Article

References (20)

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16. 6S, calculated: 479.2467; obtained: 479.2432.
17. 6S, calculated: 527.2466; obtained: 527.2429.
18. 6S, calculated: 575.2467; obtained: 575.2434.
19. 1H NMR (400 MHz) δ: 1.37, 1.52, 1.59 (3s, 3×3H, 3Me), 1.94 (d, J=5 Hz, 1H, H-3), 2.01 (s, 3H, Me-18), 2.34 (m, 2H, H-6), 2.63 (d, J=19 Hz, 1H, H-14), 3.02 (dd, J=15 and 5 Hz, 1H, H-20), 3.16 (m, 1H, H-5), 3.52 (d, J=19 Hz, 1H, H-14), 4.08 (d, J=15 Hz, 1H, H-20), 4.12 (s, 1H, OH), 4.27 (d, J=5 Hz, 1H, H-2), 4.42 (d, J=10 Hz, 1H, H-9), 4.88 (d, J=10 Hz, 1H, H-10), 5.81 (s, 1H, H-benzylidene-1,2), 6.10 (s, 1H, H-benzylidene-9,10), 7.40 (m, 5H, H-Ph), 7.43 (m, 5H, H-Ph).
20. 7S, calculated: 617.2572; obtained: 617.2584.