Synthesis of Epilupinine

Structure of Epilupinine

C10H19NO

Principal investigatorFrederick G. West
Publication year1994
Synthesis typeTotal
Number of steps 5 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Et3N
EtOAc
60 °C, ON, 80%
intermediate structure
Cu(acac)2
PhMe
Reflux, 2.5 h, 82%
"The product is a 95:5 mixture of diastereomers at C-5 (major shown). 88:12 e.r."
intermediate structure
BF3.OEt2, (CH2SH)2
RT, 48 h, 64%
intermediate structure
LiAlH4
THF
0 °C to RT, 3 h, 94%
intermediate structure
NH2NH2, Na
Ethylene Glycol
190-195 °C, 16 h, 76%
intermediate structure