Reaktion #821838

ord-233a37a0b5d24ee992c7acfd65e31822

Reaktionsgleichung

CC(C)=CCC[C@@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(=C[C@@H]4CC1C(C)(C)OC2(C/C=C(\CO)C(=O)O)C4=O)C3=O
Isogambogic acid
CC(C)=CCC[C@@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(=C[C@@H]4CC1C(C)(C)OC2(C/C=C(\CO)C(=O)O)C4=O)C3=O
30-hydroxygambogic acid
→
CC(C)=CCC[C@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(=C[C@@H]4CC1C(C)(C)OC2(C/C=C(\C)C(=O)O)C4=O)C3=O
Isogambogic Acid

Edukte

CC(C)=CCC[C@@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(=C[C@@H]4CC1C(C)(C)OC2(C/C=C(\CO)C(=O)O)C4=O)C3=O
Isogambogic acid
CC(C)=CCC[C@@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(=C[C@@H]4CC1C(C)(C)OC2(C/C=C(\CO)C(=O)O)C4=O)C3=O
30-hydroxygambogic acid
—
acid ( 2 )

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
CHCl3
ClC(Cl)Cl
CHCl3

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Isogambogic acid (1) obtained was a bright yellow amorphous powder. [α]D20=−660° (c=0.321, CHCl3). ESIMS: m/z=629 ([M+H]+); (+)FABMS: m/z=629 ([M+H]+); HRESIMS: m/z=obsd. 629.3133 [M+H]+, calcd. 629.3114. Epiisogambogic acid (2) was also a bright yellow amorphous powder. [α]D20=−587° (c=0.261, CHCl3). ESIMS: m/z=629 ([M+H]+); (+)FABMS: m/z=629 ([M+H]+); HRESIMS: m/z=obsd. 629.3101 [M+H]+, calcd. 629.3114. More analytic data are shown in the following table 5:

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07592367B2uspto-grants-2009_09