Synthesis of Retigeranic Acid

C25H38O2

Principal investigator	Tomas Hudlicky
Publication year	1988
Synthesis type	Total
Number of steps	15 (linear)
References	Tetrahedron Lett. 1988, 29, 3283.

Part 1 of 1

O3
Me2S

CH2Cl2

-78 °C, 88%

Piperidine

Et2O

0 °C

O3
Me2S

CH2Cl2

-78 °C, 30-65%

HMPA, i-Pr2NLi

THF

-78 to 0 °C, 60 min

See the Horner-Wadsworth-Emmons Reaction

Ph3P+CH3 Br-, n-BuLi

THF

66% (2 steps)

See the Wittig Reaction

								
																	PhMe															

								300 °C, 								8 h, 								23%
							
								See the Diels-Alder Reaction
							
								"The yield was 76 % brsm."

HCl

THF

RT, 30 min

LiI

DMF

Reflux, 2 h, 65% (2 steps)

See the Krapcho Decarboxylation

TMSCHBrCO2Et, i-Pr2NLi

THF

-78 °C, 70%

See the Peterson Olefination

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."