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Enantio‐ and Diastereoselective Total Synthesis of (+)‐Panepophenanthrin, a Ubiquitin‐Activating Enzyme Inhibitor, and Biological Properties of Its New Derivatives
Author(s) -
Matsuzawa Masayoshi,
Kakeya Hideaki,
Yamaguchi Junichiro,
Shoji Mitsuru,
Onose Rie,
Osada Hiroyuki,
Hayashi Yujiro
Publication year - 2006
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600199
Subject(s) - chemistry , ubiquitin , monomer , enzyme , catalysis , total synthesis , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , polymer , gene
The asymmetric total synthesis of (+)‐panepophenanthrin, an inhibitor of ubiquitin‐activating enzyme (E1), has been accomplished using catalytic asymmetric α aminoxylation of 1,4‐cyclohexanedione monoethylene ketal as a key step, followed by several diastereoselective reactions. The biomimetic Diels–Alder reaction of a monomer precursor was found to proceed efficiently in water. The investigation of the biological properties of new derivatives of (+)‐panepophenanthrin enabled us to develop new cell‐permeable E1 inhibitors, RKTS‐80, ‐81, and ‐82.