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Named reactions

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Search synthesis

Retigeranic Acid

Chemical structure of Retigeranic_Acid
C25H38O2
Author Tomas Hudlicky
Publication year 1988
Synthesis type Total synthesis
Number of steps 15 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C, 88%
Chemical structure
Piperidine
Et2O
0 °C
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C, 30-65%
Chemical structure + Chemical structure
i-Pr2NLi, HMPA
THF
-78 to 0 °C, 60 min

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
Ph3P+CH3 Br-, n-BuLi
THF
66% (2 steps)

See the Wittig Reaction
Chemical structure
PhMe
300 °C, 8 h, 23%

Selectivity : 75:25
See the Diels-Alder Reaction
The yield was 76 % brsm.
Chemical structure
+
Chemical structure
HCl
THF
RT, 30 min
Chemical structure
LiI
DMF
Reflux, 2 h, 65% (2 steps)

See the Krapcho Decarboxylation
Chemical structure
TMSCHBrCO2Et, i-Pr2NLi
THF
-78 °C, 70%

See the Peterson Olefination
Chemical structure + Chemical structure
i-Pr2NLi
THF
-100 to -78 °C, 50%

Selectivity : 50:50
See the Michael Addition
For the synthesis of this enone, see : J. Am. Chem. Soc. 1984, 106, 6690.
Chemical structure
PbCO3
10-6 mmHg
585 °C, 55-60%

Also isolated was the C5b-epimer (20 % yield).
Chemical structure
NaBH4
MeOH
Chemical structure
  1. NaH
  2. CS2
  3. MeI
THF
Chemical structure
n-Bu3SnH, AIBN
PhMe
72% (3 steps)

See the Barton-McCombie Reaction
Chemical structure
KOH
MeOH, H2O
Chemical structure

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