Claims
- 1. A process for synthesizing taxol comprising the following steps:
- Step A: providing an activated A ring intermediate represented by the following structure: ##STR4## Step B: providing an activated C ring intermediate represented by the following structure: ##STR5## Step C: producing a bicyclic AC ring intermediate by attaching the activated C.sup.1 of the activated A ring intermediate of said Step A to the activated C.sup.2 of the activated C ring intermediate of said Step B, the bicyclic AC ring intermediate being represented by the following structure: ##STR6## then; Step D: activating the bicyclic AC ring intermediate of said Step C for producing an activated bicyclic AC ring intermediate having an activated C.sup.9 and an activated C.sup.10, the activated bicyclic AC ring intermediate being represented by the following structure: ##STR7## then; Step E: producing a tricyclic ABC ring intermediate by annulating the activated bicyclic AC ring intermediate of said Step D by bonding the activated C.sup.9 to the activated C.sup.10, the tricyclic ABC ring intermediate being represented by the following structure: ##STR8## then; Step F: activating the tricyclic ABC ring intermediate of said Step E for producing an activated tricyclic ABC ring intermediate having an activated C.sup.5 and an activated .sup.20, the activated tricyclic ABC ring intermediate being represented by the following structure: ##STR9## and then; Step G: producing taxol by forming an oxygen linkage between the activated C.sup.5 and the activated C.sup.20 of the activated tricyclic ABC ring intermediate of said Step F, taxol being represented by the following structure: ##STR10##
CROSS-REFERENCE TO RELATED APPLICATION
The present application is a continuation-in-part of U.S. patent application Ser. No. 08/193,263, filed Feb. 8, 1994, which is a continuation-in-part of U.S. patent application Ser. No. 08/110,095, filed Aug. 20, 1993 now U.S. Pat. No. 5,440,057 and is a continuation-in-part of U.S. patent application Ser. No. 08/141,847, filed Oct. 22, 1993 now abandoned, which is a continuation-in-part of U.S. patent application Ser. No. 08/064,810, filed May 19, 1993 now abandoned, which is a divisional of U.S. patent application Ser. No. 07/902,390, filed Jun. 23, 1992 now U.S. Pat. No. 5,274,137, the disclosures of which is incorporated herein by reference.
GOVERNMENT RIGHTS
The invention disclosed herein was supported in part by Grant Number CA46446 from the National Institutes of Health. The United States government may have certain rights to this invention.
Non-Patent Literature Citations (7)
Entry |
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). |
Divisions (1)
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902390 |
Jun 1992 |
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Continuation in Parts (3)
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193263 |
Feb 1994 |
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Parent |
110095 |
Aug 1993 |
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64810 |
May 1993 |
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