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
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- i-Pr2NLi
- MeO2CCN
THF
-100 to 0 °C, 80 min, 90%

Part 2 of 3
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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
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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."
