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Synthese und Charakterisierung der 8 isomeren, im Ring B mono‐ bzw. dihydroxylierten Royleanone
Author(s) -
Meier Heidi,
Rüedi Peter,
Eugster Conrad Hans
Publication year - 1981
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.19810640304
Subject(s) - chemistry , ring (chemistry) , stereochemistry , quinone , medicinal chemistry , organic chemistry
Synthesis and Characterization of the 8 Stereoisomeric Royleanones with One or Two Hydroxy Groups in Ring B The partial syntheses of 6α, 7α‐dihydroxyroyleanone ( 6a ), 6α, 7β‐dihydroxyroyleanone ( 7a ) and 6β, 7β‐dihydroxyroyleanone ( 9a ) are described. Thus, all in ring B mono‐ and dihydroxylated royleanones are now known (see [2–11]), being fully characterized by extensive spectroscopic, chiroptic and chromatographic (HPLC.) methods. An opening of the epoxyroyleanone 11a yields cis ‐ and trans ‐diols together with their corresponding mono‐ and di‐ O ‐acetyl derivatives. We postulate a reversible addition of the acetate ion at C(8) of the quinone system, followed by a neighbouring group participation of this O ‐acetyl group.