Synthesis of Retigeranic Acid

Structure of Retigeranic Acid

C25H38O2

Principal investigator	Elias J. Corey
Publication year	1985
Synthesis type	Total
Number of steps	27 (linear)
References	J. Am. Chem. Soc. 1985, 107, 4339.

Part 1 of 1

intermediate structure

LiAlH4

Et2O

-20 °C, 90 min, 99%

intermediate structure

DEAD, Ph3P, BzOH

Et2O

-25 °C, 60 min

See the Mitsunobu Reaction

intermediate structure

KOH

MeOH

RT, 15 h, 89% (2 steps)

intermediate structure

Special reagent

H2

65 atm

THF

RT, 6.5 h

intermediate structure

CrO3, H2SO4

Acetone, H2O

93% (2 steps)

See the Jones Oxidation

intermediate structure

VinylMgBr

Et2O

0 °C, 97%

See the Grignard Reaction

intermediate structure

KHSO4

40 mmHg

150 °C, 82%

intermediate structure

+

intermediate structure

98-105 °C, 120 h, 61%

See the Diels-Alder Reaction

intermediate structure

+

intermediate structure

TMS2NK

PhMe

RT, 12 h, 80%

See the Wittig Reaction

intermediate structure

LiAlH4

Et2O

0 °C, 30 min, 99%

intermediate structure

n-Bu3P, o-NO2PhSeCN

THF

RT, 60 min

intermediate structure

Me2S, mCPBA

CH2Cl2

-78 °C to RT, 15 h, 75% (2 steps)

See the Grieco Dehydration

intermediate structure

H2SO4

H2O, MeOH

RT, 100%

intermediate structure

(COCl)2

PhH

RT, 2 h

intermediate structure

Et3N

PhH

RT, 5 min, 80% (2 steps)

intermediate structure

MeCH(SMe)2, n-BuLi

THF

-78 °C, 73%

See the Corey-Seebach Reaction

intermediate structure

Et3N, CuOTf

PhH

RT, 10 min

intermediate structure

NaIO4

Dioxane , H2O

RT, 12 h

intermediate structure

Al(Hg)

H2O, THF

0 °C to RT, 3 h, 65% (3 steps)

intermediate structure

H2, Pd/C

1 atm

Pyr, THF

RT, 24 h, 83%

intermediate structure

NaOMe

MeOH

-78 °C, 89%

intermediate structure

TsN3

EtOH

RT, 12 h

intermediate structure

Catecholborane, n-Bu4N+ OAc-

CHCl3

RT to 65 °C, 90 min, 83% (2 steps)

intermediate structure

OsO4

Pyr

RT, 60 min

intermediate structure

Pb(OAc)4

CH2Cl2

-78 to 0 °C, 30 min, 69% (2 steps)

See the Criegee Reaction

intermediate structure

Al2O3

4 Å MS

CH2Cl2

RT, 2 h, 70%

See the Aldol Condensation

intermediate structure

NaH2PO4, NaClO2, 2-Methyl-2-butene

H2O, t-BuOH

RT, 30 min, 85%

See the Pinnick-Lindgren Oxidation

intermediate structure

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