Premium
Synthesis of heterocyclic compounds related to fredericamycin A – the cyclopent[ g ]isoquinoline system
Author(s) -
Clive Derrick L. J.,
Sedgeworth Janette
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240240
Subject(s) - isoquinoline , chemistry , pyridine , conjugate , stereochemistry , base (topology) , product (mathematics) , combinatorial chemistry , organic chemistry , mathematical analysis , geometry , mathematics
Abstract A synthetic route is described to compounds 9 and 10 , which resemble the cyclopent[ g ]isoquinoline system of the antitumor agent, Fredericamycin A. The method is based upon directed lithiation of the pyridine 6 and conjugate addition to 2‐cyclopenten‐1‐one. Cyclization of the product 7 with base then generates the required skeleton, which can be aromatized and methylated (7 → 8 → 9).