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Named reactions

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Search synthesis

Retigeranic Acid

Chemical structure of Retigeranic_Acid
C25H38O2
Author Leo A. Paquette
Publication year 1987
Synthesis type Total synthesis
Number of steps 29 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
NaH, KH
PhMe
Reflux, 20 h, 66%
Chemical structure
  1. O3
  2. Me2S
MeOH
-78 °C to RT, 79%
Chemical structure
NaH
PhMe
Reflux, 18.5 h, 66%

See the Aldol Condensation
Chemical structure
LiI.3H2O
DMF
Reflux, 18 h, 85%

See the Krapcho Decarboxylation
Chemical structure + Chemical structure
CuBr.Me2S
THF, Me2S
-78 to 0 °C, 24 h

See the Michael Addition
Chemical structure
HCl
Acetone, H2O
RT, 3 d, 72% (2 steps)

See the Aldol Addition
Chemical structure
ClC(S)O(p-MePh)
Pyr
RT, ON, 73%
Chemical structure
24 mmHg
180 °C, 60 min, 99%

See the Chugaev Elimination
Chemical structure
NH2NH2.H2O, K2CO3
Diethylene glycol
150 to 200 °C, 7 h, 72%

See the Wolff-Kishner Reduction
Chemical structure
Na2CrO4
AcOH, Ac2O
0 °C to RT, 24 h, 64%
Chemical structure

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Part 2 of 3
Chemical structure
i-Bu2AlH
100%
Chemical structure
KH, n-Bu3SnCH2I
Chemical structure
n-BuLi
75% (2 steps)

See the Wittig Rearrangement-[2,3]
Chemical structure
  1. O3
  2. Me2S
70%
Chemical structure
TBSCl, Imidazole
DMF
85%
Chemical structure
i-Bu2AlH
100%
Chemical structure
POCl3
Pyr
40-45 °C, 75%
Chemical structure
CrO3, 3,5-Dimethylpyrazole
CH2Cl2
49%
Chemical structure
VinylMgBr, CuBr.Me2S
50%

See the Michael Addition
Also isolate was the C3-epimer (15 % yield).
Chemical structure
NH2NH2.H2O, K2CO3
Diethylene glycol
190 °C, 73%

See the Wolff-Kishner Reduction
Chemical structure
Ph3P, DEAD, ZnBr2
THF
RT, 91%

See the Mitsunobu Reaction
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Mg
Et2O
Reflux, 13%

See the Michael Addition
Also isolated was the C3-epimer (40 % yield).
Chemical structure
  1. O3
  2. Me2S
Chemical structure
Piperidine, AcOH
PhMe
Reflux, 48 h, 41%

Selectivity : 80:20 R/S
See the Claisen-Schmidt Condensation
Chemical structure
H2, PtO2
5 atm
AcOH, THF
86%
Chemical structure
TMSCN, KCN, 18-Crown-6
6800 atm
Chemical structure
POCl3, DBU
Pyr
Reflux, 30%
Chemical structure
i-Bu2AlH
Chemical structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
t-BuOH, H2O
56% (2 steps)

See the Pinnick-Lindgren Oxidation
Chemical structure

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