Synthesis of Kendomydin
C29H42O6
Principal investigator | Johann Mulzer |
---|---|
Publication year | 2009 |
Synthesis type | Total |
Number of steps | 39 (7 parts) |
References |
Part 1 of 7
- Sn(OTf)2
- Acrolein
CH2Cl2, Et3N
-20 °C, 60 min, 91%
"87:17 d.r."
LiOH,
H2O2
H2O, THF
RT, 1 h, 72%
Me2C(OMe)2,
Camphorsulfonic acid
RT, ON, 91%
LiAlH4
Et2O
0 °C, 30 min, 96%
Part 2 of 7
H5IO6
Et2O
0 °C
LiAlH4
Et2O
0 °C, 3 h, 77% (3 steps)
Imidazole,
TBDPSCl
DMF
0 °C to RT, 1 h, 90%
- O3
- Ph3P
CH2Cl2
-78 to 0 °C, 2 h, 99%
- Cp2ZrHCl
- I2
THF
-78 to 0 °C, 1 h, 76%
Part 3 of 7
PhI(OAc)2
H2O, MeOH
RT, 16.5 h
Na2S2O4
Et2O, H2O
RT, 3 h, 72% (2 steps)
MeOCH2Cl,
NaH
THF
0 °C to RT, 24 h, 94%
NBS
THF
0 °C, 16 h, 89%
Part 4 of 7
+
DMDO
Acetone
RT, 15 min, 99%
TfOH
4A MS
EtOH, PhMe
80 °C, 5 min, 95%
NaH,
MeOCH2Cl
DMF
RT, 1 h, 95%
n-Bu4N+ F-
THF
RT, ON, 89%
IBX
DMSO
RT, 2 h, 97%
Part 5 of 7
+
Et2O
-78 °C, 52%
"d.r. 50:1, 86% ee"
Part 6 of 7
+
DMAP,
EDC
CH2Cl2
RT, 81%
TBSCl,
TMS2NLi
HMPA, THF
-78 °C to RT
uW
DMF
180 °C, 10 min
LiAlH4
Et2O
0 °C, 89%
MsCl
CH2Cl2
0 °C
LiAlH4
Et2O
0 °C, 89%
Part 7 of 7
+
n-BuLi,
(CH2NMe2)2
THF
-78 to -25 °C, 3.5 h, 90%
"76:24 S/R at C6"
N2(COOK)2,
AcOH
CH2Cl2
reflux, 36 h, 60%
HCl
H2O, MeOH
RT, 4 h, 96%
TESOTf,
Et3N
CH2Cl2
0 °C to RT, ON, 82%
IBX
DMF
RT, 24 h
HF
H2O, MeCN
RT, 4 h, 30% (2 steps)