TY - JOUR
T1 - Naphtho[2,3-c]furan-4,9-dione and a Further Exploratory Approach to the Ring System of Ventilone A
AU - Karichiappan, K.
AU - Wege, Dieter
PY - 2000
Y1 - 2000
N2 - 1,4-Dimethoxy-2,3-didehydronaphthalene (10), generated by the dehydrobromination of 2-bromo-1,4-dimethoxynaphthalene (9), was trapped with furan and 2-methylfuran, and the resulting adducts were converted into naphtho[2,3-c]furan-4,9-dione (1) and 1-methylnaphtho[2,3-c]furan-4,9-dione (19) respectively. An attempt to extend this procedure to the synthesis of ventilone A (2) failed when the adduct (31), derived from 6,7-methylenedioxy-1,4,5,8- tetramethoxy-2,3-didehydronaphthalene (30) and 2-methylfuran, could not be oxidized selectively.
AB - 1,4-Dimethoxy-2,3-didehydronaphthalene (10), generated by the dehydrobromination of 2-bromo-1,4-dimethoxynaphthalene (9), was trapped with furan and 2-methylfuran, and the resulting adducts were converted into naphtho[2,3-c]furan-4,9-dione (1) and 1-methylnaphtho[2,3-c]furan-4,9-dione (19) respectively. An attempt to extend this procedure to the synthesis of ventilone A (2) failed when the adduct (31), derived from 6,7-methylenedioxy-1,4,5,8- tetramethoxy-2,3-didehydronaphthalene (30) and 2-methylfuran, could not be oxidized selectively.
U2 - 10.1071/CH00056
DO - 10.1071/CH00056
M3 - Article
SN - 0004-9425
VL - 53
SP - 743
EP - 747
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 2000
ER -