Synthesis of Maritimol
C20H34O2
| Principal investigator | Pierre Deslongchamps |
|---|---|
| Publication year | 2000 |
| Synthesis type | Formal |
| Number of steps | 26 (3 parts) |
| References |
Part 1 of 3
+
+
- i-Pr2NLi
- MeO2CCN
THF
-100 to 0 °C, 80 min, 90%
Part 2 of 3
+
+
Me2SO4,
NaH
DMSO
5 °C to RT, 4 h, 87%
- O3
- Me2S
- NaBH4
CH2Cl2, MeOH
-78 °C to RT, 5 h, 73%
TBSCl,
Imidazole,
DMAP
CH2Cl2
0 °C, 60 min, 95%
NaOH
H2O, THF
5 °C, ON, 96%
NHMeOMe,
CDI,
Et3N
CH2Cl2
0 °C to RT, ON, 89%
i-Bu2AlH
CH2Cl2
-78 °C, 6 h, 89%
+
Pyr.TsOH
PhH
Reflux, 48 h, 93%
TBDPSCl,
Imidazole
CH2Cl2
RT, 30 min, 100%
+
i-Pr2NLi
-100 to 0 °C, 2 d, 83%
MMPP
Et2O, MeOH
0 °C, 5 min, 98%
Pyr.HF
THF
RT, 15 min, 76%
Part 3 of 3
+
+
CsI,
Cs2CO3
Syringe pump
MeCN
80 °C, 14 h, 73%
n-Bu4N+ F-
THF
0 °C to RT, 3 h, 87%
B(Oi-Pr)3,
TMSCH2CN,
n-BuLi
THF
-78 °C, 90 min, 67%
See the Peterson Olefination
"Also isolated was the E-isomer (12 % yield)."
Pd/C,
H2
1 atm
AcOH, EtOAc
RT, 4 h, 87%
H3PO4
AcOH, H2O
110 °C, 37 h, 68%
Pt/C,
H2
40 atm
EtOAc
RT, 3 h
Remaining...
43% (2 steps)
"See: Can. J. Chem. 1985, 63, 3418."