Synthesis of Tunicamycin V

Structure of Tunicamycin V

C38H62N4O16

Principal investigatorAndrew G. Myers
Publication year1993
Synthesis typeTotal
Number of steps 28 (5 parts)
References
Part 1 of 5
intermediate structure
KF.2H2O
MeOH
RT, 6.5 h, 100%
intermediate structure
K2CO3, Cl3CCN
CH2Cl2
RT, 24 h, 64%
intermediate structure
Part 2 of 5
intermediate structure
BrCCl3
hv
0 °C, 2.5 h, 87%
intermediate structure
i-Pr2NEt, BnOCH2Cl
CH2Cl2
Reflux, 15 h, 89%
intermediate structure
PhSeH, Et3N
0 to 60 °C, 2.5 h, 98%
intermediate structure
Phthaloyl Chloride, Et3N, DBU
CH2Cl2, PhMe
0 to 100 °C, 100 min, 86%
intermediate structure
PhSeH, Et3N
DME
90 °C, 10 h, 95%
intermediate structure
Et3N.3HF
MeCN
RT, 6 h, 97%
intermediate structure
Part 3 of 5
intermediate structure + intermediate structure
TfOH
4A MS
PhMe
-20 °C, 24 h, 77%
intermediate structure
NH2NH2.H2O
EtOH
100 °C, 12 h, 87%
intermediate structure
ClCO2Bn
Pyr
0 °C, 30 min, 91%
intermediate structure
PhSeH
Et3N
55 °C, 12 h, 91%
intermediate structure
Ac2O
Pyr
60 °C, 2.5 h, 91%
intermediate structure
mCPBA
CCl4
-15 to 0 °C, 50 min, 88%
intermediate structure
K2CO3, NaOH
RT, 2 h, 92%
intermediate structure
Part 4 of 5
intermediate structure
DMAP, Et3N, TMSCl
CH2Cl2
RT, 2 h
"DMT = Dimethoxytrityl"
intermediate structure
DMAP, Boc2O
Pyr
RT, 12 h
intermediate structure
KF.2H2O
MeOH
RT, 3 h, 79% (3 steps)
intermediate structure
ClCO2Allyl
Pyr
-20 to RT, 35 min, 87%
intermediate structure
PhSO3H
CHCl3
RT, 2 min, 76%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 20 min, 72%
intermediate structure
Part 5 of 5
intermediate structure + intermediate structure
  1. PhSeH
  2. Me2SiCl2
PhMe, Pyr
RT, 6 h, 81%
intermediate structure
Pd(PPh3)2Cl2, n-Bu3SnH
CH2Cl2, H2O
RT, 6 min, 85%
intermediate structure
Et3B, n-Bu3SnH
0 °C, 2 h
intermediate structure
KF.2H2O
MeOH
RT, 2 h, 60% (2 steps)
intermediate structure
Pd, HCO2H
MeOH
RT to 40 °C, 6.5 h
intermediate structure
HF
H2O, MeCN, MeOH
RT, 2 h
intermediate structure
Special reagent
DCC
CH2Cl2, MeOH
RT, 2 d, 83% (3 steps)
intermediate structure