Synthesis of Retigeranic Acid

Structure of Retigeranic Acid

C25H38O2

Principal investigatorTomas Hudlicky
Publication year1988
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C, , 88%
intermediate structure
Piperidine
Et2O
0 °C
intermediate structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C, , 30-65%
intermediate structure + intermediate structure
i-Pr2NLi, HMPA
THF
-78 to 0 °C, 60 min
intermediate structure
Ph3P+CH3 Br-, n-BuLi
THF
66% (2 steps)
See the Wittig Reaction
intermediate structure
PhMe
300 °C, 8 h, 23%
"The yield was 76 % brsm."
intermediate structure + intermediate structure
HCl
THF
RT, 30 min
intermediate structure
LiI
DMF
Reflux, 2 h, 65% (2 steps)
intermediate structure
TMSCHBrCO2Et, i-Pr2NLi
THF
-78 °C, , 70%
intermediate structure + intermediate structure
i-Pr2NLi
THF
-100 to -78 °C, , 50%
"For the synthesis of this enone, see : J. Am. Chem. Soc. 1984, 106, 6690."
intermediate structure
PbCO3
585 °C, , 55-60%
"Also isolated was the C5b-epimer (20 % yield)."
intermediate structure
NaBH4
MeOH
intermediate structure
  1. NaH
  2. CS2
  3. MeI
THF
intermediate structure
n-Bu3SnH, AIBN
PhMe
72% (3 steps)
intermediate structure
KOH
MeOH, H2O
intermediate structure