Synthesis of Tirandamycin B

Structure of Tirandamycin B

C22H27NO8

Principal investigatorPhilip DeShong
Publication year1991
Synthesis typeTotal
Number of steps 18 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
CrCl3, LiAlH4
THF
0 °C to RT, 5 h, 30%
"Also isolated was the C2-epimer (47 % yield)."
intermediate structure
TBSCl, Imidazole
DMF
RT, 5 d, 82%
intermediate structure
O3
CH2Cl2
-78 °C
intermediate structure
Zn, AcOH
Et2O, H2O
RT, 2 h, 95% (2 steps)
intermediate structure + intermediate structure
t-BuLi, (CH2NMe2)2
Et2O
-78 to 0 °C, 4 h, 42%
"Also isolated was the C1-epimer (42 % yield)."
intermediate structure
mCPBA
CH2Cl2
RT, 3 h, 89%
intermediate structure
HF, H2SiF6
MeCN, H2O
RT, 20 min, 35%
intermediate structure
NaBH4, CeCl3
MeOH
RT, 5 min, 99%
See the Luche Reduction
intermediate structure
mCPBA, Na3PO4
CH2Cl2, H2O
RT, 24 h, 73%
intermediate structure
Li.DTBBP
THF
-78 °C, 3 h, 95%
intermediate structure
H2Cr2O7.2Pyr
CH2Cl2
RT, 7 h, 85%
intermediate structure + intermediate structure
CrCl3, LiAlH4
THF
0 °C to RT, 3 h, 81%
intermediate structure
OsO4, NaIO4
Dioxane , t-BuOH, H2O
RT, 7 h, 85%
intermediate structure
TsOH
PhH
Reflux, 2 h, 75%
intermediate structure + intermediate structure
KOt-Bu
THF
0 °C, 18 h, 72%
intermediate structure
CF3CO2H
RT, 5 min, 98%
intermediate structure
n-Bu4N+ F-
THF
RT, 21 h
intermediate structure
PhMe
Reflux, , 91% (2 steps)
intermediate structure