Synthesis of (±)-camptothecin using a [3+2] nitrone cycloaddition to construct the CDE ring moiety

Tetrahedron Letters

Volumn 45, Issue 39, 2004, Pages 7247-7250

  Yu, Jurong ^a   Depue, Jeffrey ^a   Kronenthal, David ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

3+2 Nitrone cycloaddition; Camptothecin; CDE ring moiety; Synthesis

Indexed keywords

CAMPTOTHECIN; NITRONE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG SYNTHESIS; MOLECULAR INTERACTION; POLYMERIZATION; REACTION ANALYSIS;

EID: 4444249603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.025     Document Type: Article

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28. 3 resulted in over-reduction of 13
29. The major by-products were 21 and 22 with the combination of these impurities typically comprising greater than 20% of the total reaction mixture.
30. 3) δ 8.43 (s, 1H), 8.24 (d, J = 8 Hz, 1H), 7.95 (d, J = 8 Hz, 1H), 7.90 (s, 1H), 7.85 (t, J = 8 Hz, 1H), 7.70 (t, J = 8 Hz, 1H), 5.38 (d, J = 23.8 Hz, 1H), 5.32 (d, J = 23.8 Hz, 1H), 3.85-4.00 (m, 1H), 3.45-3.55 (m, 1H), 3.25-3.35 (m, 1H), 3.15-3.25 (m, 1H), 2.42-2.52 (m, 1H), 2.17-2.28 (m, 1H), 1.26 (t, J = 9 Hz, 3H), 1.15 (t, J = 9 Hz, 3H), 0.92 (t, J = 9 Hz, 3H)