Synthesis of Ziziphine N

Structure of Ziziphine N

C33H49N5O6

Principal investigatorDawei Ma
Publication year2007
Synthesis typeTotal
Number of steps 17 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
DCC, DMAP
CH2Cl2
0 °C to RT, 3 h
intermediate structure
MeOH
Reflux, 40 min
intermediate structure
NaBH4
CH2Cl2
0 °C, 8 h, 50% (3 steps)
intermediate structure
BH3.Me2S
THF
Reflux, 4 h, 90%
intermediate structure
Part 2 of 3
intermediate structure
NaOH, CHCl3
EtOH, H2O
70 °C, 3 h, 41%
intermediate structure
K2CO3, MeI
DMF
RT, 60 min, 87%
intermediate structure
TMS2NLi, Ph3P+CH2I I-
HMPA, THF
-78 °C to RT, 60 min
See the Wittig Reaction
intermediate structure
Pyr.TsOH
MeOH
RT, , 56% (2 steps)
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
DIAD, Ph3P
THF
80 °C, 3 h, 54%
intermediate structure
CuI, Cs2CO3, Me2NCH2CO2H.HCl
Dioxane
80 °C, 12 h, 75%
intermediate structure
n-Bu4N+ F-
THF
RT, , 95%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 2 h
intermediate structure
NaH2PO4, NaClO2, 2-Methyl-2-butene
MeCN, t-BuOH
0 °C to RT
intermediate structure
Pd(PPh3)4, Me2NH
CH2Cl2
RT, 50 min, 56% (3 steps)
intermediate structure
i-Pr2NEt, Ph2P(O)OC6F5
DMF
RT, 24 h, 66%
intermediate structure
ZnBr2
CH2Cl2
0 °C, 4 h
intermediate structure + intermediate structure
K2CO3
DMF
0 °C, ON, 22% (2 steps)
intermediate structure