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US 7,126,000 B2Granted
Method of synthesizing camptothecin-relating compounds
AssigneeKabushiki Kaisha Yakult Honsha
InventorsTakanori Ogawa, Hiroyuki Nishiyama, Miyuki Uchida, Seigo Sawada
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Abstract
The present invention is to prepare efficiently 2′-amino-5′-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.
Claims27
A process for preparing a tricyclic ketone to synthesize camptothecin analogs, wherein from Compound (k):
- (wherein TMS is a trimethylsilyl group, and Me is a methyl group), or Compound (v):
- (wherein TMS is a trimethylsilyl group, and Me is a methyl group), Compound (l):
- (wherein TMS is a trimethylsilyl group, and Me is a methyl group)
- is produced;
- and from Compound (l) Compound (m):
- (wherein TMS is a trimethylsilyl group, and Me is a methyl group)
- is produced;
- and from Compound (m) Compound (n):
- (wherein TMS is a trimethylsilyl group, Me is a methyl group, and Et is an ethyl group)
- is produced;
- and from Compound (n) Compound (o):
- (wherein TMS is a trimethylsilyl group, Me is a methyl group, and Et is an ethyl group)
- is produced;
- and from Compound (o) Compound (p):
- (wherein TMS is a trimethylsilyl group, Me is a methyl group, and Et is an ethyl group)
- is produced;
- and from Compound (p) Compound (q):
- (wherein Me is a methyl group, and Et is an ethyl group)
- is produced;
- and from Compound (q) Compound (r):
- (wherein Me is a methyl group, Et is an ethyl group, and Pr is a propyl group)
- is produced;
- and from Compound (r) Compound (s):
- (wherein Et is an ethyl group, and Pr is a propyl group)
- is produced;
- and from Compound (s) Compound (t):
- (wherein Et is an ethyl group, and tBu is a t-butyl group)
- is produced;
- and from Compound (t) Compound (h):
- (wherein Et is an ethyl group)
- is produced, wherein the improvement comprises
- (1) a step to obtain Compound (l) that comprises mixing Compound (k), a lithiating agent, a formylation reagent and an iodination reagent.
29 more elements
Dependencies are inferred from the claim text.