Intermediates in the synthesis of (+) camptothecin and related c

Details Intermediates in the synthesis of (+) camptothecin and related c Intermediates in the synthesis of (+) camptothecin and related c

1996-03-04

1998-04-28

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544343, 546302, C07D48704, C07D47114, C07D21364, C07B 3710

Patent

active

057446059

ABSTRACT:
The present method provides a short, convergent total synthesis of novel intermediates in the synthesis of (.+-.)-camptothecin and related compounds. The synthesis scheme includes a novel 4+1 radical annulation followed by another cyclization to simultaneously assemble rings B and C of the Camptothecin compound. In the synthesis, the following novel precursor is reacted with a phenyl isocyanide: ##STR1## The resulting tetracyclic intermediates comprise a quinoline fused to a pyrrolidine ring, with the pyrrolidine ring being fused to an alpha-pyridone ring. The tetracyclic intermediates thus comprise the A, B, C, and D rings characteristic of camptothecin and camptothecin derivatives, and are easily convertible to camptothecin and camptothecin derivatives via hydroxymethylation and oxidation.

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Gottlieb, Cancer Chemotheraps Reports Part 1 vol. 56, p. 103 (1972).
Moertel, Cancer Thoms. Reporst Part 1 vol. 56, p. 95 (1972).

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