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Named reactions

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Pseudolaric Acid B

Chemical structure of Pseudolaric_Acid_B
C23H28O8
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
Chemical structure
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
Chemical structure
TBSCl, Imidazole, DMAP
DMF
RT, 14 h
Chemical structure
i-Bu2AlH
PhMe
-78 °C, 60 min
Chemical structure
  1. TMSCHN2, i-Pr2NLi
  2. TMSCl
THF
-78 to 0 °C, 11 h, 73% (3 steps)
Chemical structure
Ph3P, I2, Imidazole
PhMe
RT, 60 min, 90%

See the Appel Reaction
Chemical structure

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Part 2 of 3
Chemical structure
TBDPSCl, Imidazole
THF
RT, 18 h, 92%
Chemical structure
Reagent structure
Et2Zn, CH2I2
CH2Cl2, DME
-10 °C to RT, 14.5 h, 91%

Selectivity : >95:05 er
See the Charette Asymmetric Cyclopropanation
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 5.5 h, 100%

See the Swern Oxidation
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
  1. Ph3P+CH3 Br-, PhLi, LiBr
  2. HCl
  3. KOt-Bu
THF, MeOH
-78 °C to RT, 18 min

See the Schlosser Modification
Chemical structure
K2CO3
CH2Cl2, MeOH
RT, 21 h, 58% (2 steps)
Chemical structure
Reagent structure
DCE
0 °C to RT, 90 min, 88%

Selectivity : 94:06 dr
Chemical structure
n-Bu4N+ F-
THF
0 °C to RT, 4 h, 94%
Chemical structure
TESCl, Imidazole, DMAP
DMF
0 °C to RT, 16 h, 85%
Chemical structure
mCPBA, NaHCO3
CH2Cl2
-20 °C, 30 min

See the Prilezhaev Reaction
Chemical structure
i-Pr2NLi
THF
-10 °C, 40 min, 72% (2 steps)
Chemical structure
DDQ
CH2Cl2, Buffer (pH = 7)
0 °C, 15 min
Chemical structure
MnO2, KCN, AcOH
MeOH
RT, 10 h, 85% (2 steps)
Chemical structure
n-Bu4N+ F-, AcOH
THF
RT, 18 h, 87%
Chemical structure
CDI
THF
RT, 24 h, 100%
Chemical structure
(PhSe)2, NaBH4
DMF
RT, 8 h, 92%
Chemical structure
Cl3C(=NH)OCH2(p-MeOPh), Sc(OTf)3
PhMe
0 °C, 2 h, 94%
Chemical structure
n-Bu3SnH, DCC, DBU
PhH
RT to 70 °C, 20 h, 85%
Chemical structure
  1. KOTMS
  2. Me2SO4, TsOH, i-Pr2NEt
µW
PhMe, MeOH
100 to 120 °C, 45 min
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
0 °C, 60 min, 59% (2 steps)

See the Dess-Martin Oxidation
The yield was 73 % brsm.
Chemical structure
DDQ
CH2Cl2, Buffer (pH = 7)
0 °C to RT, 60 min, 76%
Chemical structure + Chemical structure
CeCl3, LiCl, n-BuLi
THF
-78 °C, 2.5 h, 87%

Selectivity : >95:05 dr
The yield was 98 % brsm.
Chemical structure
[(Bu2SnNCS)2O]2
µW
PhMe
130 °C, 30 min, 94%
Chemical structure
n-Bu4N+ F-
THF
0 °C to RT, 20 min, 87%
Chemical structure
Sc(OTf)3
Ac2O
0 °C, 2 h, 98%
Chemical structure
n-Bu3SnH, Pd(PPh3)2Cl2
THF
RT, 15 min, 90%
Chemical structure + Chemical structure
Pd2(dba)3, i-Pr2NEt
NMP
RT, 22 h, 62%

See the Stille Coupling
Chemical structure

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