Synthesis of Thielocin A1b

C54H60O18
Principal investigator | Robert N. Young |
---|---|
Publication year | 2001 |
Synthesis type | Total |
Number of steps | 21 (4 parts) |
References |
Part 1 of 4


H2SO4,
Cl3CCH2OH
RT, 5 d, 61%

K2CO3,
Me2SO4
Acetone
50 °C, 3 h, 90%

Et3SiH
CF3CO2H
RT, 15 h, 96%

Part 2 of 4

NaBH3CN,
Piperidine
AcOH, MeCN
RT, 83%

NaH,
TBSCl
Et3N
RT, 95%

MeOTf
CH2Cl2
0 °C to RT, 30 min, 99%

Part 3 of 4


TMS(CH2)2OH,
NaH
PhH
120 °C, 4 h, 63%

TBDPSCl,
Et3N,
DMAP
CH2Cl2
RT, 96 h, 91%

PhI(OAc)2
AcOH
RT, 5 h, 57%

LiOH,
12-Crown-4
H2O, THF
RT, 15 h, 70%

Part 4 of 4
+


n-Bu4N+ F-
DMF, THF
-20 °C to RT, 3.5 h, 95%

CDI
Et3N
RT, 1 h, 98%

n-Bu4N+ F-
DMF, THF
RT, 15 h, 67%

MeOCHCl2
CH2Cl2
Reflux, 3 h


Et3N
CH2Cl2
RT, 15 h, 83 % (2 steps)

Cd
AcOH, DMF
RT, 15 h, 84 %


(CF3CO)2O
PhH
RT, 15 h, 83%

Cd
AcOH, DMF
RT, 15 h, 80%

NaOH
Dioxane , H2O
-10 °C, 8-10 h, 59%
