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Synthesis of 1,2,3,12a,12b‐Hexahydrocyclopropa‐[1,2‐ d ]benzo[ f ]pyrrolo[1,2‐ b ]isoquinolin‐5,7‐dione related to duocarmycins and anthramycin
Author(s) -
Venkatram Atigadda,
Colley Tara,
Deruiter Jack,
Smith Forrest
Publication year - 2005
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.5570420220
Subject(s) - chemistry , aryne , diastereomer , imine , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Structural features of the Duocarmycins and Anthramycin were incorporated into 1,2,3,12a,12b‐hexahydro‐cyclopropa[1,2‐ d ]benzo[ f ]pyrrolo[1,2‐ b ]isoquinolin 5,7‐dione. The synthesis of the cis and trans diastereomers was accomplished using a benzyne Diels‐Alder reaction and an imine‐anhydride cyclization as key steps.