Synthesis of Maritimol

Structure of Maritimol

C20H34O2

Principal investigatorPierre Deslongchamps
Publication year2000
Synthesis typeFormal
Number of steps 26 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
CrCl2, LiI
THF, DMF
RT, ON, 75%
See the Takai Reaction
intermediate structure
  1. i-Pr2NLi
  2. MeO2CCN
THF
-100 to 0 °C, 80 min, 90%
intermediate structure
Part 2 of 3
intermediate structure
Me2SO4, NaH
DMSO
5 °C to RT, 4 h, 87%
intermediate structure
  1. O3
  2. Me2S
  3. NaBH4
CH2Cl2, MeOH
-78 °C to RT, 5 h, 73%
intermediate structure
TBSCl, Imidazole, DMAP
CH2Cl2
0 °C, 60 min, 95%
intermediate structure
NaOH
THF, H2O
5 °C, ON, 96%
intermediate structure
CDI, NHMeOMe, Et3N
CH2Cl2
0 °C to RT, ON, 89%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 6 h, 89%
intermediate structure + intermediate structure
Pyr.TsOH
PhH
Reflux, 48 h, 93%
intermediate structure
TBDPSCl, Imidazole
CH2Cl2
RT, 30 min, 100%
intermediate structure + intermediate structure
i-Pr2NLi
-100 to 0 °C, 2 d, 83%
intermediate structure
MMPP
MeOH, Et2O
0 °C, 5 min, 98%
intermediate structure
Pyr.HF
THF
RT, 15 min, 76%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
PdCl2.2MeCN
DMF
RT, ON, 68%
See the Stille Coupling
intermediate structure
Cl3CC(O)CCl3, Ph3P
CH2Cl2
-78 to 0 °C, 15 min, 94%
See the Appel Reaction
intermediate structure
Cs2CO3, CsI
MeCN
80 °C, 14 h, 73%
intermediate structure
n-Bu4N+ F-
THF
0 °C to RT, 3 h, 87%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
0 °C, 60 min, 91%
intermediate structure
H2O
DMSO
155 °C, 3.5 h, 86%
intermediate structure
TMSCH2CN, n-BuLi, B(Oi-Pr)3
THF
-78 °C, 90 min, 67%
"Also isolated was the E-isomer (12 % yield)."
intermediate structure
H2, Pd/C
EtOAc, AcOH
RT, 4 h, 87%
intermediate structure
KOt-Bu
t-BuOH
85 °C, 2.5 h, 100%
intermediate structure
H3PO4
AcOH, H2O
110 °C, 37 h, 68%
intermediate structure
H2, Pt/C
EtOAc
RT, 3 h
intermediate structure
Dess-Martin Periodinane
CH2Cl2
0 °C to RT, 10 h, 84% (2 steps)
intermediate structure
Remaining...
43% (2 steps)
"See: Can. J. Chem. 1985, 63, 3418."
intermediate structure