Synthesis of Retigeranic Acid

C25H38O2
Principal investigator | Tomas Hudlicky |
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Publication year | 1988 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1
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- O3
- Me2S
CH2Cl2
-78 °C, 88%

Piperidine
Et2O
0 °C

- O3
- Me2S
CH2Cl2
-78 °C, 30-65%






HCl
THF
RT, 30 min




i-Pr2NLi
THF
-100 to -78 °C, 50%
See the Michael Addition
"For the synthesis of this enone, see : J. Am. Chem. Soc. 1984, 106, 6690."

PbCO3
10<sup>-6</sup> mmHg
585 °C, 55-60%
"Also isolated was the C5b-epimer (20 % yield)."

NaBH4
MeOH

- NaH
- CS2
- MeI
THF


KOH
H2O, MeOH
