Synthesis of Maoecrystal V
C19H22O5
| Principal investigator | Phil S. Baran |
|---|---|
| Publication year | 2016 |
| Synthesis type | Total |
| Number of steps | 18 (3 parts) |
| References |
Part 1 of 3
- NaH
- TMS2NH
- MeI
THF
0 °C to Reflux, 4.5 h, 79%
Br2
CHCl3
0 °C, 2 h, 70%
MgO
DMF
140 °C, 3 h, 49%
I2,
Pyr
CCl4
RT, 12 h, 75%
Part 2 of 3
+
+
CuI.Me2S
PhMe, 2-MeTHF
-78 °C, 4.5 h, 80%
">99:01 e.r."
- LiTMP
- Ac2O
THF, DMPU
-78 to 0 °C, 3.5 h, 64%
- NaH , n-Bu4N+ I- , Me2SO4
- H2O , LiOH
DMF
0 °C to RT, 7 h
Part 3 of 3
+
+
- LaCl3.2LiCl , TMS2NNa
- (CH2O)n
THF, DMPU
-45 °C, 3 h, 56%
See the Aldol Addition
"Also isolated was the C1-epimer (28% yield)"
CF3CO2H,
HC(OMe)3
MeOH
60 °C, 3 h
Zn(OTf)2,
LiBH4
CH2Cl2, THF
RT, 50 h, 62% (2 steps)
"Also isolated was the C6'-epimer (21% yield)"
- TsOH , H2O , Et3N
- 3,5-Dinitrobenzoyl chloride , DMAP
CH2Cl2, THF
0 °C to RT, 14 h, 86%
HC(OMe)3,
MsOH
MeOH
RT to 55 °C, 40 h
- TMSCN , ZnI2
- LiOH , H2O
- HCl
THF
RT to 65 °C, 5 h, 82% (2 steps)
DMDO
Acetone
RT, 24 h
- InI3 , MgI2
- Dess-Martin Periodinane
- n-Bu4N+ HSO4- , Oxone , K2CO3 , H2O , Rochelle salt
MeCN, Buffer (pH = 7.4)
0 °C to RT, 29 h, 76% (2 steps)