Synthesis of Sarain A
C32H50N2O3
| Principal investigator | Larry E. Overman |
|---|---|
| Publication year | 2007 |
| Synthesis type | Total |
| Number of steps | 51 (3 parts) |
| References |
Part 1 of 3
+
NaBH4,
BH3.Me2S
THF
0 °C to RT, 26 h, 54%
Imidazole,
TBDPSCl
THF
0 °C to RT, 52 h, 82%
H2,
Pd/C
1 atm
EtOAc
RT, 24 h
+
CH2Cl2
RT, 24 h, 73% (2 steps)
Part 2 of 3
- n-BuLi
- ClCO2Me
THF
-78 °C to RT, 92%
H2,
Lindlar Catalyst
1 atm
PhMe
RT, 3 h, 99%
Part 3 of 3
+
+
+
+
+
+
+
+
DMSO
180 °C, 60 min, 69%
AlMe3
PhMe
RT, 90 min, 91%
- TMS2NLi
- AllylBr
THF, DMPU
-78 to -55 °C, 25 h, 92%
HCl
H2O, THF
RT, 48 h, 98%
Boc2O,
DMAP
MeCN
RT, 15 h, 96%
i-Bu2AlH
CH2Cl2
-78 °C, 25 min
NaBH3CN
AcOH
RT, 12 h, 93% (2 steps)
DMSO
130 °C, 4.5 h
n-Bu4N+ F-,
Ac2O
Et3N, THF
70 °C, 16 h
"R = H or Ac (mixture)"
K2CO3
MeOH
RT, 12 h, 68% (3 steps)
"R = H or Ac (mixture)"
i-Bu2AlH
CH2Cl2
-78 °C, 5 h, 87%
NaOMe
THF
0 °C to RT, 4 h
+
Et3N,
Triphosgene
CH2Cl2
0 °C, 45 min, 92% (2 steps)
- O3 , NaHCO3
- Me2S
CH2Cl2, MeOH
-78 °C to RT, 12 h, 92%
+
HF
H2O, MeCN
91% (2 steps)
TIPSOTf,
Et3N
CH2Cl2
-78 °C to RT, 12 h, 97%
TBSCl,
Imidazole
MeCN
RT, 2 h
NaBH4
MeOH
0 °C, 2 h
TIPSOTf,
Et3N
CH2Cl2
RT, 48 h, 75% (3 steps)
Naphtalene,
Na
DME, THF
-78 °C, 84%
+
NaBH3CN,
AcOH
4 Å MS
MeCN
RT, 25 min, 94%
Pd/C,
H2
1 atm
EtOAc
RT, 6 h, 82% (2 steps)
HCl
H2O, THF
RT, 6 h, 95%
- TMS2NNa
- (4-MeOPh)CH2Cl
DMF
RT, 30 min, 89%
TASF
DMA
100 °C, 60 min
KOH
EtOH
90 °C, 12 h, 65% (2 steps)
+
PhH
80 °C, 3 h, 86%
IBX
DMSO
RT, 105 min, 71%
+
n-Bu4N+ F-
THF
RT, 105 min, 85%
TESCl,
Imidazole
DMF
0 °C, 15 min, 70%
K2CO3
MeOH
0 °C to RT, 13 h, 92%
+
i-Bu2AlH
PhMe
-78 to 0 °C, 25 min, 64% (2 steps)
Pyr.HF
CH2Cl2
0 °C, 90 min, 49% (2 steps)