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Cover Picture: Synthesis of the Aglycone of the Argelosides: Antiproliferative 14,15‐ seco ‐Pregnane Glycosides (Asian J. Org. Chem. 3/2014)
Author(s) -
Tamiya Minoru,
Isaka Nobuhisa,
Kitazawa Takaki,
Ishiguro Masaji
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201490004
Subject(s) - pregnane , chemistry , aglycone , sharpless asymmetric dihydroxylation , dihydroxylation , stereochemistry , wacker process , glycoside , combinatorial chemistry , enantioselective synthesis , organic chemistry , palladium , catalysis
Highly oxygenated steroidal derivatives are important targets in biology and chemistry. In their Communication on page 264 ff., Minoru Tamiya and co‐workers accomplished the synthesis of the aglycon of the argelosides, a highly‐oxygenated seco ‐pregnane with cage‐like D, E, and F rings, through the three oxidative operations: 1) Sharpless asymmetric dihydroxylation, 2) Baeyer‐Villiger oxidation, and 3) Wacker oxidation. Despite the rather simple strategy, the major challenge lay in handling the easy‐to‐aromatize structure in the intermediate and target molecules.