Synthesis of Murrayazoline

C23H25NO

Principal investigator	Noritaka Chida
Publication year	2008
Synthesis type	Total
Number of steps	22 (3 parts)
References	Org. Lett. 2008, 10, 1999.

Part 1 of 3

Et3N, TsCl

CH2Cl2

0 °C, 4 h

NIS

DMF

0 °C to RT, 60 min, 76% (2 steps)

Pd(PPh3)4, Na2CO3

EtOH, H2O, PhH

Reflux, 3 h, 99%

See the Suzuki Coupling

NaNO2 , H2SO4
CuBr , HBr

AcOH, H2O

0 to 80 °C, 14 h, 92%

See the Sandmeyer Reaction

NaOMe

MeOH

Reflux, 8 h

MeOCH2Cl, NaH

DMF

0 °C to RT, 90 min, 92% (2 steps)

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Part 2 of 3

TMS2NK, Ph3P+CH2OMe Cl-

PhMe

0 to 120 °C, 4 h

See the Wittig Reaction

HCl

H2O, THF

RT, 12 h, 74% (2 steps)

MeLi

Et2O

-78 °C, 60 min, 92%

n-Pr4N+ RuO4-, NMO

4 Å MS

CH2Cl2

RT, 30 min, 85%

See the Ley-Griffith Oxidation

MeLi

Et2O

-78 °C, 2 h, 64%

TMSN3, TsOH, BF3.OEt2

PhH

0 °C, 30 min

Me3O+BF4-, CuSO4

CH2Cl2, H2O

0 °C to RT, 14 h, 61% (2 steps)

TMSCl, TMS2NK, Et3N

THF

-78 °C, 40 min

Pd(OAc)2

MeCN

RT, 4 h, 84% (2 steps)

See the Saegusa-Ito Oxidation

(TMSOCH2)2, TMSOTf

CH2Cl2

-78 to -15 °C, 90 min, 99%

LiAlH4

THF

0 °C, 2 h, 87%

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Part 3 of 3

Pd2(dba)3, NaOt-Bu

Sealed tube

PhMe

130 °C, 13 h, 59%

See the Buchwald-Hartwig Coupling

Sc(OTf)3Sealed tube

																	DCE, 																	H2O															

								120 °C, 								36 h, 								73%
							
								See the Friedel-Crafts Alkylation
							
								See the Michael Addition

DMAP, Et3N, Tf2O

CH2Cl2

0 °C, 60 min, 94%

MeMgBr

Et2O

0 °C, 60 min, 77%

See the Grignard Reaction

Pd(OAc)2

Sealed tube

PhMe

120 °C, 20 h, 80%

See the Buchwald-Hartwig Coupling

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