Synthesis of Stigmatellin A

C30H42O7
Principal investigator | Dieter Enders |
---|---|
Publication year | 2000 |
Synthesis type | Total |
Number of steps | 22 (4 parts) |
References |
Part 1 of 4



HCl
H2O, MeOH
Reflux, 2 h, 99%

i-Pr2NEt,
MeOCH2Cl
CH2Cl2
0 °C to RT, ON, 98%

Part 2 of 4
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+




i-Pr2NLi
Et2O
-100 °C to RT, ON, 80%

MMPP
MeOH, Buffer (pH = 7)
-15 °C, 15 min, 87%





(NH4)2Ce(NO3)6
H2O, MeCN
0 °C, 6 min, 90%

H2Cr2O7.2Pyr
DMF
RT, ON, 100%

Part 3 of 4
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i-Bu2AlH
Et2O
-78 °C, 60 min, 99%

PBr3
Et2O
0 °C, ON, 93%


Part 4 of 4
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+


DMAP,
t-BuCOCl,
i-Pr2NEt
CH2Cl2
RT, 3.5 h, 57%


Pd/C,
H2
1 atm
MeOH
RT, 6 min, 74%



