Synthesis of Kinamycin F

C18H14N2O7
Principal investigator | Kyriacos C. Nicolaou |
---|---|
Publication year | 2007 |
Synthesis type | Total |
Number of steps | 27 (3 parts) |
References |
Part 1 of 3
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AgNO3,
(NH4)2S2O8
H2O, MeCN
65 °C, 3.5 h, 75%

Ag2O,
BnBr
CH2Cl2
RT, 18 h, 92%

Na2S2O4
Et2O, EtOAc, H2O
RT, 30 min


KOt-Bu
THF
0 °C, 2 h, 98%


Part 2 of 3

- CuBr.Me2S , MeMgBr
- TMSCl
HMPA, THF
-78 °C to RT, 2.5 h
See the Michael Addition
"The starting material was 90:10 er."


OsO4,
NMO
Acetone, H2O
RT, 45 min, 76%
See the Upjohn Dihydroxylation
"Cristallized thrice to >99:01 er."

2-Methoxypropene,
Camphorsulfonic acid
THF
RT, 18 h, 95%

- TMS2NLi
- TMSCl
THF
0 °C, 30 min


I2
CH2Cl2, Pyr
RT, 30 min, 92%

Part 3 of 3
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Ac2O,
DMAP,
Et3N
CH2Cl2
RT, 20 h, 95%

SmI2,
MeOH
THF
-78 °C, 10 min

Et3N
CH2Cl2
RT, 60 min, 81% (2 steps)

SeO2
Dioxane
110 °C, 9 h, 72%

HF
H2O, MeCN
RT, 3 h

DMAP,
Et3N,
Ac2O
CH2Cl2
RT, 20 min, 89% (2 steps)

H2,
Pd/C
1 atm
AcOH, EtOAc
RT, 3 h, 99%

Imidazole,
TBSCl
DMF
RT, 3 h, 94%

HCl,
TsNHNH2
H2O, i-PrOH
RT, 18 h, 95%

(NH4)2Ce(NO3)6
MeCN, Buffer (pH = 7)
0 °C, 60 min, 42%

HCl
H2O, MeCN
RT, 3 h, 95%

LiOH
H2O, THF
RT, 60 min, 92%
