Practical total synthesis of (+)-Camptothecin: The full story

Tetrahedron

Volumn 53, Issue 32, 1997, Pages 11049-11060

  Ciufolini, Marco A ^a   Roschangar, Frank ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030796897     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00365-7     Document Type: Article

References (77)

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32. The term "cycloaddition" is used throughout this paper to indicate the gross outcome of particular reactions. No mechanistic inferences should be drawn from this usage, particularly with respect to issues of concertedness.
33. The pyridine-forming reaction has been reviewed in detail: Ciufolini, M. A., in Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, ch. 1.
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35. These values were obtained by extended Hückel molecular orbital calculations performed on MM+ geometries. All calculations were carried out with the Hyperchem® package, version 4, available from Hypercube, Inc., Ontario, Canada, and running on a pentium / 100 PC system.
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38. Prepared according to Hoff, S.; Brandsma, L.; Arens, J. F. Rec. Trav. Chim. Pays-Bas 1968, 87, 916.
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63. Maximum enantioselectivity is obtained with PLE in 25 % aq. DMSO: Andrade, M. A. C.; Andrade, F. A. C.; Phillips, R. S. Bioorg. Med. Chem. Lett. 1991, 1, 373. The MOM group promotes high enantioselectivity and fast rate of hydrolysis: Luyten, M.; Müller, S.; Herzog, B.; Keese, R. Helv. Chim. Acta 1987, 70, 1250.
64. Maximum enantioselectivity is obtained with PLE in 25 % aq. DMSO: Andrade, M. A. C.; Andrade, F. A. C.; Phillips, R. S. Bioorg. Med. Chem. Lett. 1991, 1, 373. The MOM group promotes high enantioselectivity and fast rate of hydrolysis: Luyten, M.; Müller, S.; Herzog, B.; Keese, R. Helv. Chim. Acta 1987, 70, 1250.
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76. Natural CPT was purchased from Aldrich and obtained as a gift from Dr. Monroe E. Wall, Research Triangle Institute, NC.
77. 2. All other reagents and solvents were used as received. Microanalyses were performed at Galbraith Laboratories, Knoxville, TN.