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Synthesis of several deoxy analogues of pancratistatin
Author(s) -
Balázs LÁSzlÓ,
Kádas István,
Tõke László
Publication year - 1998
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.5570350215
Subject(s) - chemistry , dihydroxylation , osmium tetroxide , column chromatography , catalysis , organic chemistry , osmium , stereochemistry , enantioselective synthesis , ruthenium , electron microscope , physics , optics
N ‐Acetylated 1,4,7‐ and 3,4,7‐trideoxypancratistatin analogues 10 and 13 were synthesised from partially saturated phenanthridinones, 6 and 7 , respectively via epoxidation and trans opening of the epoxides. Compounds 16 and 17 , cis analogues of 13 were also synthesised from 7 via cis dihydroxylation with catalytic osmium tetroxide and N ‐methylmorpholine N ‐oxide. The stereoisomers obtained were separated by column chromatography after protection of the hydroxyl groups. The products synthesised are characterised satisfactorily by ir, nmr, ms and microanalysis data and are expected to possess anticancer or antiviral activity.