Total synthesis of taxol and taxol analogs

Details Total synthesis of taxol and taxol analogs Total synthesis of taxol and taxol analogs

1994-02-16

1995-10-24

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549511, C07D30514

Patent

active

054611695

ABSTRACT:
The total synthesis of taxol employs a convergent synthetic plan. The synthetic plan may also be employed to produce a large number of taxol analogs. Taxol analogs having skeletal extensions are inaccessible by modification of the natural product but are readily produced by employing the convergent synthetic plan herein.

REFERENCES:
McMurry, J. "Carbonyl-Coupling Reactions Using Low-Valent Titanium", Chem. Rev., 89: 1513-1524 (1989).
Nicolaou, et al. "Novel Chemistry of Taxol, Retrosynthetic and Synthetic Studies", J. Chem. Soc. Chem. Comm., 295-296 (1994).
Chamberlin, et al. "Lithioalkanes from Arene-Sufonyl Hydrazones", Organic Reactions, 39: 1-83 (1990).
Ojima, et al. "New and Efficient Approches to the Semisynthesis of Taxol and its C-13 Side Chain Analogs By Means of .beta.-Lactam Synthon Method" Tetrahearon, 48: 6985-7012 (1992).
Nicolaou, et al. "Synthesis of ABC Taxoid Ring Systems via a Convergent Stategy", J. Chem. Soc. Chem. Comm. 1024-1025 (1993).
Nicolaou, et. al. "Synthesis of a Fully Functionalized CD Ring System of Taxol", J. Chem. Soc. Chem. Comm, 1118-1119 (1992).
Nicolaou, et. al. "A Convergent Synthesis Toward Taxol. A Facile Enantioselective Entry Into a Fully Functionalized Ring A System", J. Chem. Soc. Chom. Comm, 1117-1118 (1992).

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