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Pseudolaric Acid B
| Author | Barry M. Trost |
|---|---|
| Publication year | 2007 |
| Synthesis type | Total synthesis |
| Number of steps | 31 (3 parts) |
| Reference |
Browse hundreds of other total syntheses.
Part 1 of 3
H2, [RuI2(p-cymene)]2, (R)-BINAP
120 atm
MeOH, CH2Cl2
40 °C, 24 h, 95 %
Selectivity : >95:05 er
See the Noyori Asymmetric Hydrogenation
120 atm
40 °C, 24 h, 95 %
Selectivity : >95:05 er
See the Noyori Asymmetric Hydrogenation
TBSCl, Imidazole, DMAP
DMF
RT, 14 h
RT, 14 h
i-Bu2AlH
PhMe
-78 °C, 60 min
-78 °C, 60 min
TMSCHN2, i-Pr2NLi, TMSCl
THF
-78 to 0 °C, 11 h, 73 % (3 steps)
-78 to 0 °C, 11 h, 73 % (3 steps)
Part 2 of 3
TBDPSCl, Imidazole
THF
RT, 18 h, 92 %
RT, 18 h, 92 %
Et2Zn, CH2I2
-10 °C to RT, 14.5 h, 91 %
Selectivity : >95:05 er
See the Charette Asymmetric Cyclopropanation
Part 3 of 3
+ 
K2CO3
CH2Cl2, MeOH
RT, 21 h, 58 % (2 steps)
RT, 21 h, 58 % (2 steps)
0 °C to RT, 90 min, 88 %
Selectivity : 94:06 dr
n-Bu4N+ F-
THF
0 °C to RT, 4 h, 94 %
0 °C to RT, 4 h, 94 %
TESCl, Imidazole, DMAP
DMF
0 °C to RT, 16 h, 85 %
0 °C to RT, 16 h, 85 %
i-Pr2NLi
THF
-10 °C, 40 min, 72 % (2 steps)
-10 °C, 40 min, 72 % (2 steps)
DDQ
CH2Cl2, Buffer (pH = 7)
0 °C, 15 min
0 °C, 15 min
MnO2, KCN, AcOH
MeOH
RT, 10 h, 85 % (2 steps)
RT, 10 h, 85 % (2 steps)
n-Bu4N+ F-, AcOH
THF
RT, 18 h, 87 %
RT, 18 h, 87 %
CDI
THF
RT, 24 h, 100 %
RT, 24 h, 100 %
(PhSe)2, NaBH4
DMF
RT, 8 h, 92 %
RT, 8 h, 92 %
Cl3C(=NH)OCH2(p-MeOPh), Sc(OTf)3
PhMe
0 °C, 2 h, 94 %
0 °C, 2 h, 94 %
n-Bu3SnH, DCC, DBU
PhH
RT to 70 °C, 20 h, 85 %
RT to 70 °C, 20 h, 85 %
KOTMS, Me2SO4, TsOH, i-Pr2NEt
µW
PhMe, MeOH
100 to 120 °C, 45 min
µW
100 to 120 °C, 45 min
Dess-Martin Periodinane, NaHCO3
CH2Cl2
0 °C, 60 min, 59 % (2 steps)
See the Dess-Martin Oxidation
The yield was 73 % brsm.
0 °C, 60 min, 59 % (2 steps)
See the Dess-Martin Oxidation
The yield was 73 % brsm.
DDQ
CH2Cl2, Buffer (pH = 7)
0 °C to RT, 60 min, 76 %
0 °C to RT, 60 min, 76 %
+ 
CeCl3, LiCl, n-BuLi
THF
-78 °C, 2.5 h, 87 %
Selectivity : >95:05 dr
The yield was 98 % brsm.
-78 °C, 2.5 h, 87 %
Selectivity : >95:05 dr
The yield was 98 % brsm.
[(Bu2SnNCS)2O]2
µW
PhMe
130 °C, 30 min, 94 %
µW
130 °C, 30 min, 94 %
n-Bu4N+ F-
THF
0 °C to RT, 20 min, 87 %
0 °C to RT, 20 min, 87 %
Sc(OTf)3
Ac2O
0 °C, 2 h, 98 %
0 °C, 2 h, 98 %
n-Bu3SnH, Pd(PPh3)2Cl2
THF
RT, 15 min, 90 %
RT, 15 min, 90 %
+ 
