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Die Konstitution des Loroglossins. 163. Mitt. über organische Naturstoffe
Author(s) -
Gray Robert W.,
Guggisberg Armin,
Segebarth Klaus Peter,
Hesse Manfred,
Schmid Hans
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600419
Subject(s) - chemistry , diazomethane , diastereomer , acetylation , hydrolysis , glucoside , pyridinium , organic chemistry , tartrate , stereochemistry , medicinal chemistry , medicine , biochemistry , alternative medicine , pathology , gene
The Constitution of Loroglossine Loroglossine, a characteristic constituent of orchids, is shown to be bis[4‐(β‐ D ‐glucopyranosyloxy)‐benzyl]‐(2 R , 3 S )‐2‐isobutyl‐tartrate (1) . Base catalysed hydrolysis and esterification with diazomethane gave 1 mol‐equiv. of dimethyl (+)‐2‐isobutyl‐erythro‐tartrate ((+)‐ 3 ) and 2 mol‐equiv. of a glucoside which after acetylation formed 4 identical with a synthetic sample. The structure of (+)‐ 3 follows from the synthesis of (±)‐ 3 by osmium tetroxide oxidation of isobutyl‐maleic acid anhydride and subsequent esterification. The absolute configuration of (+)‐ 3 was based on Horeau experiments and NMR. data of the diastereomeric mixture of its esters 15 and 16 and pure 15 with ( S )‐(+)‐ and ( R )‐(−)‐α‐phenyl‐butyric acid, respectively.