Über die Konstitution von Loroglossin. Vorläufige Mitteilung

✍ Scribed by Robert W. Gray; Armin Guggisberg; Klaus Peter Segebarth; Manfred Hesse; Hans Schmid

• Publisher: John Wiley and Sons
• Year: 1976
• Tongue: German
• Weight: 307 KB
• Volume: 59
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19760590229

✦ Synopsis

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). Hydrolysis and esterification gave 1 mol‐equiv. of dimethyl (+)‐2‐isobutyl‐erythro‐tartrate ((+)‐3) and 2 mol.‐equiv. of a glucoside which, after acetylation, gave 4, identical with a synthetic sample. The erythro configuration of (+)‐3 by oxidation of isobutyl‐maleic acid with osmium tetroxide and subsequent esterification. The absolute configuration of (+)‐3 was based on Horeau experiments and NMR. data of the diastereomeric mixture of its esters 7 and 8 with S (+)‐ and R (−)‐α‐phenylbutyric acid respectively.