Synthesis of Citreofuran

Structure of Citreofuran

C16H16O5

Principal investigator	Alois Fürstner
Publication year	2003
Synthesis type	Total
Number of steps	13 (3 parts)
References	J. Org. Chem. 2003, 68, 1521.

Part 1 of 3

intermediate structure

NaH
n-BuLi
HCl , H2O

THF

-78 °C to Reflux, 42 h, 67%

See the Claisen Condensation

intermediate structure

LiOH, Me2SO4

THF

50 °C, 3 h, 86%

See the Williamson Ether Synthesis

intermediate structure

NaOH

H2O, MeOH

60 °C, 24 h, 97%

intermediate structure

TMS(CH2)2OH, Ph3P, DIAD

THF

0 °C to RT, 3.5 h, 85%

See the Mitsunobu Reaction

intermediate structure

i-Pr2NLi
CO2

THF

-78 °C, 40 min, 85%

intermediate structure

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Part 2 of 3

intermediate structure

+

intermediate structure

THF, DMPU

-20 °C to RT, 22.5 h, 52%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

DCC, DMAP

CH2Cl2

RT, ON, 94%

See the Steglich Esterification

intermediate structure

n-Bu4N+ F-

THF

RT, ON, 95%

intermediate structure

Special reagent

Et3N

THF

RT, 2.5 h

intermediate structure

Special reagent

TMSCl
H2O , NH4Cl

THF

-78 °C to RT, 3.5 h, 75% (2 steps)

See the Grignard Reaction

intermediate structure

(t-BuO)3WCCMe3

PhMe

85 °C, 60 min, 78%

See the Alkyne Metathesis

intermediate structure

TsOH

PhMe

85 °C, 5.5 h, 85%

intermediate structure

B-I-9-BBN

CH2Cl2

-10 °C, 4 h, 60%

intermediate structure

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