K. Tachibana, M. Tori, Y. Moriyama
Jun 1, 1977
Citations
0
Influential Citations
11
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
3β,4β-Epoxyshionane (15) was treated with boron trifluoride etherate in ether at −30 °C to give dihydrobaccharis oxide (4; yield 17%), 4α-fluoroshionan-3β-ol (17; 10%), D: B-friedo-bacchar-5-en-3β-ol (18; 18%), D:B-friedo-bacchar-5(10)-en-3β-ol (20; 15%), and D: C-friedo-bacchar-7-en-3β-ol (21; 15%). The reaction in benzene, toluene, cyclohexane, or in hexane at −5 °C or at room temperature yielded bacchar-12-en-3β-ol (5), D: C-friedo-bacchar-8-en-3β-ol (25), 18, 20, and 21. The reaction product ratios in the same reaction in various solvents are listed in Table 1.