Synthesis of Platensimycin
C24H27NO7
| Principal investigator | Martin J. Lear |
|---|---|
| Publication year | 2014 |
| Synthesis type | Total |
| Number of steps | 27 (3 parts) |
| References |
Part 1 of 3
AcOH, PPA
75-80 °C, 2 h, 69%
BnBr,
K2CO3,
n-Bu4N+ I-
DMF
55 °C, 12 h, 95%
H2,
Pd/C
1 atm
MeOH
RT, 16 h, 92%
Part 2 of 3
BnBr,
K2CO3,
n-Bu4N+ I-
DMF
55 °C, 16 h, 99%
NaIO4
H2O, THF
RT, 4 h
LiAlH4
THF
-10 °C to RT, 2 h, 88%
t-BuOOH,
Ti(Oi-Pr)4,
(+)-DIPT
4A MS
CH2Cl2
-30 °C to RT, 7.5 h, 98%
See the Sharpless Epoxidation
"91% ee"
AllylMgBr
THF
-40 °C to RT, 110 min, 93%
n-Bu2SnO,
TsCl,
Et3N
CH2Cl2
RT, 3 h, 99%
NaIO4
H2O, THF
RT, 2 h, 85% (2 steps)
H2,
Pd/C
1 atm
THF
RT, 2.5 h
n-Bu4N+ F-
THF, Xylene(s)
reflux, 4 h, 86% (2 steps)
Dioxane
60 °C, 130 h
H2,
KOH,
Pd/C
1 atm
EtOAc, EtOH
RT, 90 min, 58% (2 steps)
"Also islated was C9 epimer (15%)"
AlCl3,
n-Bu4N+ I-
CH2Cl2, MeCN
-1 °C, 20 h, 83%
Et3N,
MsCl
CH2Cl2
0 °C, 6 h
LiBr,
Li2CO3
DMSO
150 °C, 4 h, 72% (2 steps)
- TMS2NK
- MeI
HMPA, THF
-78 to -10 °C, 3.5 h, 80%
CF3CO2H
CH2Cl2
0 °C, 12 h, 100%
"91:09 dr"
Part 3 of 3
+
+
Et3N,
HATU
DMF
RT, 25 h, 71%
KOH
Dioxane , H2O, MeOH
35 °C, 16 h, 60%