Conversion of grayanotoxin III to grayanotoxin V, rhodojaponin III and rhodojaponin IV

Conversion of grayanotoxin III to grayanotoxin V, rhodojaponin III and rhodojaponin IV

Treatment of grayanotoxin (G) III with CH3CHO in the presence of anhydrous CuSO4 afforded a diethylidene compound (2). Oxidation of 2 (CrO3) and subsequent ozonolysis and hydrolysis (KOH-MeOH) gave G-V (4) in 34% overall yield. Direct ozonolysis of 2 produced rhodojaponin (R) IV (8) in 68% yield. Δ2...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1978/05/25, Vol.26(5), pp.1615-1619
Hauptverfasser: Terai, T, Katai, M, Hamanaka, N, Matsumoto, T, Meguri, H
Format: Artikel
Sprache:eng
Schlagworte:
horticultural crops
plant biochemistry
plant physiology
selective masking and demasking of grayanoids
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Zusammenfassung:Treatment of grayanotoxin (G) III with CH3CHO in the presence of anhydrous CuSO4 afforded a diethylidene compound (2). Oxidation of 2 (CrO3) and subsequent ozonolysis and hydrolysis (KOH-MeOH) gave G-V (4) in 34% overall yield. Direct ozonolysis of 2 produced rhodojaponin (R) IV (8) in 68% yield. Δ2-Diethylidene compoud (10) was oxidized to 11, which on ozonolysis-hydrolysis furnished R-III (12) in 9.2% overall yield.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.26.1615