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Synthese von rac ‐4 β‐Hydroxyobovatachromen
Author(s) -
Bohlmann Ferdinand,
Paul Axel H. K.
Publication year - 1984
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198419840713
Subject(s) - chemistry , dehydrogenation , osmium tetroxide , benzaldehyde , chalcone , ozonolysis , ring (chemistry) , condensation , derivative (finance) , medicinal chemistry , osmium , quinone , benzofuran , stereochemistry , organic chemistry , catalysis , electron microscope , physics , financial economics , optics , economics , ruthenium , thermodynamics
Synthesis of rac ‐4β‐Hydroxyobovatachromene 4 β‐Hydroxyobovatachromene ( 12 ), a 3,4‐ cis ‐flavandiol derivative isolated from Marschallia species was synthesized starting with isoevodionol ( 2 ) and 4‐hydroxybenzaldehyde. Condensation of dihydroisoevodionol ( 1 ) with 4‐(tetrahydropyranyloxy)benzaldehyde ( 3 ) furnished the chalcone 4 which, on reductive cyclization, afforded the flavene 6 . Oxidation with osmium tetroxide and dehydrogenation of the dimethyldihydropyran ring with 2,3‐dichloro‐5,6‐dicyano1,4‐quinone and subsequent cleavage of the protection groups furnished racemic 4 β‐hydroxy‐obovatachromene ( 12 ).