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Synthesis of Hydroquinoid C ‐ and O ‐Biphenyl Disaccharides by Chromium‐Templated Benzannulation Reactions
Author(s) -
Janes Erik,
Nieger Martin,
Saarenketo Pauli,
Dötz Karl Heinz
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300083
Subject(s) - chemistry , chromium , biphenyl , monosaccharide , aldol condensation , yield (engineering) , organic chemistry , benzaldehyde , condensation reaction , glucoside , aldose , mannose , fructose , glycoside , medicinal chemistry , catalysis , medicine , materials science , alternative medicine , pathology , metallurgy
Organometallic monosaccharides 6 − 10 containing a chromium styrylcarbene skeleton have been synthesized in quantitative yield from O ‐glycoside methylcarbene complexes 1 − 5 bearing diisopropylidene‐protected glucose, mannose, galactose, or fructose in a trans ‐selective aldol condensation with benzaldehyde. These compounds undergo a chromium‐templated benzannulation upon reaction with ethynyl glucoside to give diastereoisomeric mixtures of Cr(CO) 3 complexes. The differences in their thermodynamic stability was exploited in a diastereoselective synthesis of hydroquinoid biphenyl disaccharides 12 − 16 in 67−88% yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)