Synthesis of Phyllantidine

Structure of Phyllantidine

C13H15NO3

Principal investigatorMichael A. Kerr
Publication year2006
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure + intermediate structure
Yb(OTf)3
PhMe
RT to Reflux, ON, 86%
intermediate structure
LiCl
DMSO, H2O
160 °C, 2 h, 85%
intermediate structure
TMS2NK
THF
-78 °C, 2.5 h, 80 &
intermediate structure
LiAlH4
THF
0 °C, 2 h, 97%
"The major diastereoisomer was separated via its acetonide in (52 % yield)."
intermediate structure
IBX
DMSO
RT, 2 h, 64%
intermediate structure
VinylMgBr
THF
0 °C, 3 h, 76%
intermediate structure
IBX
DMSO
RT, 2 h, 79%
intermediate structure
Grubbs catalyst (2nd gen.)
CH2Cl2
Reflux, 2 h, 74%
intermediate structure + intermediate structure
DCC
CH2Cl2
RT, 60 min, 71%
intermediate structure
K2CO3, 18-Crown-6
PhMe
RT, 2.5 h, 100%
intermediate structure
DDQ
CH2Cl2, H2O
RT, ON, 98%
intermediate structure
DIAD, Ph3P
PhH
RT, ON, 98%
intermediate structure