Synthesis of Platensimycin

Structure of Platensimycin

C24H27NO7

Principal investigatorMartin J. Lear
Publication year2014
Synthesis typeTotal
Number of steps 27 (3 parts)
References
Part 1 of 3
intermediate structure
AcOH, PPA
75-80 °C, 2 h, 69%
intermediate structure
BnBr, K2CO3, n-Bu4N+ I-
DMF
55 °C, 12 h, 95%
intermediate structure
NaOMe, t-BuOCl
MeOH
5 °C to RT, 60 min, 95%
intermediate structure
H2, Pd/C
1 atm
MeOH
RT, 16 h, 92%
intermediate structure
Part 2 of 3
intermediate structure
BnBr, K2CO3, n-Bu4N+ I-
DMF
55 °C, 16 h, 99%
intermediate structure
NMO, OsO4
H2O, t-BuOH, THF
RT, 16 h
intermediate structure
NaIO4
H2O, THF
RT, 4 h
intermediate structure
Special reagent
CH2Cl2
0 °C, 12 h, 93%
See the Wittig Reaction
intermediate structure
LiAlH4
THF
-10 °C to RT, 2 h, 88%
intermediate structure
t-BuOOH, Ti(Oi-Pr)4, (+)-DIPT
4A MS
CH2Cl2
-30 °C to RT, 7.5 h, 98%
"91% ee"
intermediate structure
AllylMgBr
THF
-40 °C to RT, 110 min, 93%
intermediate structure
n-Bu2SnO, TsCl, Et3N
CH2Cl2
RT, 3 h, 99%
intermediate structure
OsO4, NMO
H2O, t-BuOH, THF
RT, 12 h
intermediate structure
NaIO4
H2O, THF
RT, 2 h, 85% (2 steps)
intermediate structure
Bi(OTf)3, LiClO4
4A MS
CH2Cl2
RT, 4.5 h, 94%
intermediate structure
H2, Pd/C
1 atm
THF
RT, 2.5 h
intermediate structure
n-Bu4N+ F-
THF, Xylene(s)
reflux, 4 h, 86% (2 steps)
intermediate structure
Special reagent
Dioxane
60 °C, 130 h
intermediate structure
H2, KOH, Pd/C
1 atm
EtOAc, EtOH
RT, 90 min, 58% (2 steps)
"Also islated was C9 epimer (15%)"
intermediate structure
AlCl3, n-Bu4N+ I-
CH2Cl2, MeCN
-1 °C, 20 h, 83%
intermediate structure
Et3N, MsCl
CH2Cl2
0 °C, 6 h
intermediate structure
LiBr, Li2CO3
DMSO
150 °C, 4 h, 72% (2 steps)
intermediate structure
  1. TMS2NK
  2. MeI
HMPA, THF
-78 to -10 °C, 3.5 h, 80%
intermediate structure
KOt-Bu, VinylCO2t-Bu
t-BuOH, THF
-10 to 0 °C, 2 h, 62%
"91:09 dr"
intermediate structure
CF3CO2H
CH2Cl2
0 °C, 12 h, 100%
"91:09 dr"
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
Et3N, HATU
DMF
RT, 25 h, 71%
intermediate structure
KOH
Dioxane , H2O, MeOH
35 °C, 16 h, 60%
intermediate structure