Synthesis of Retigeranic Acid

C25H38O2
Principal investigator | Leo A. Paquette |
---|---|
Publication year | 1987 |
Synthesis type | Total |
Number of steps | 29 (3 parts) |
References |
Part 1 of 3
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KH,
NaH
PhMe
Reflux, 20 h, 66%

- O3
- Me2S
MeOH
-78 °C to RT, 79%






ClC(S)O(p-MePh)
Pyr
RT, ON, 73%



Na2CrO4
Ac2O, AcOH
0 °C to RT, 24 h, 64%

Part 2 of 3

i-Bu2AlH
100%

n-Bu3SnCH2I,
KH


- O3
- Me2S
70%

TBSCl,
Imidazole
DMF
85%

i-Bu2AlH
100%

POCl3
Pyr
40-45 °C, 75%

3,5-Dimethylpyrazole,
CrO3
CH2Cl2
49%




Part 3 of 3
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- O3
- Me2S


PtO2,
H2
5 atm
AcOH, THF
86%

TMSCN,
18-Crown-6,
KCN
6800 atm

POCl3,
DBU
Pyr
Reflux, 30%

i-Bu2AlH

