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Named reactions

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Retigeranic Acid

Chemical structure of Retigeranic_Acid
C25H38O2
Author Paul A. Wender
Publication year 1990
Synthesis type Total synthesis
Number of steps 23 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Pig liver esterase
Buffer (pH = 7)
20 °C, 94%

Selectivity : 90:10 er
Cristallized to >99 % ee.
Chemical structure
2,2?-Dipyridyl disulfide, Ph3P
CH2Cl2
RT, 36 h, 96%
Chemical structure + Chemical structure
Li, CuI
Et2O
-78 to 0 °C, 5 h, 90%
Chemical structure
LiAlH4
Et2O
Chemical structure
H2, Pd/C, HClO4
1 atm
EtOH
RT, 15 h, 93% (2 steps)
Chemical structure
  1. o-NO2PhSeCN, n-Bu3P
  2. H2O2, H2O
THF
84%

See the Grieco Dehydration
Chemical structure
Cyclohexane
7 h, 24%

Also isolate was a regioisomer (48 % yield) which was photoisomerized to the desired product.
Chemical structure
HCONH2
Acetone, t-BuOH
7 h

Yield not reported.
Chemical structure
KOH, MeI
DMSO
RT, 48 h, 54%

The yield was 80 % at 67 % conversion.
Chemical structure
SeO2, t-BuOOH
DCE
Reflux, 23 h, 53%
Chemical structure

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Part 2 of 3
Chemical structure
H2, (Ph3P)3RhCl
1 atm
PhH
RT, 3.5 h, 90-94%
Chemical structure
Br2
AcOH
Chemical structure
KOH
H2O

See the Grob Fragmentation
Chemical structure
Ph3P+CH3 Br-, n-BuLi
THF

See the Wittig Reaction
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
i-Pr2NLi
THF
-78 to 50 °C, 5 h

See the Aldol Addition
Chemical structure
CH(OMe)2NMe2
AcOH
Reflux, 2 h, 65% (2 steps)
Chemical structure
PhMe
250 °C, 22 h, 44%

See the Diels-Alder Reaction
Also isolate was the C14-epimer (24 % yield).
Chemical structure
mCPBA, NaOAc
CH2Cl2
RT, 24 h

See the Prilezhaev Reaction
Chemical structure
KOt-Bu
DMSO
100 °C
Chemical structure
H2, Pd/C
27 atm
PhH
RT, 14 d, 25%

Also isolated was the C2-epimer (28 % yield) and internal alkenes (43 % yield) which were recycled.
Chemical structure
LiAlH4
THF
-5 °C to RT, 14 h

Yield not reported.
Chemical structure
+
Chemical structure
HCrO3Cl.Pyr
CH2Cl2
RT, 4 h

Yield not reported.
Chemical structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
t-BuOH, H2O
RT, 30 min, 85%

See the Pinnick-Lindgren Oxidation
Chemical structure

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