Synthesis of Suaveoline

Structure of Suaveoline

C20H21N3

Principal investigator	James M. Cook
Publication year	1989
Synthesis type	Total
Number of steps	20 (linear)
References	J. Am. Chem. Soc. 1989, 111, 7504.

Part 1 of 1

intermediate structure

MeI, Na

NH3

intermediate structure

HCl

MeOH

Reflux

See the Fischer-Speier Esterification

intermediate structure

NaBH4, PhCHO

MeOH

73% (3 steps)

intermediate structure

+

intermediate structure

Dioxane , PhH

Reflux

See the Pictet-Spengler Reaction

intermediate structure

HCl

MeOH

Reflux, 88% (2 steps)

See the Fischer-Speier Esterification

intermediate structure

NaH

MeOH, PhMe

Reflux

See the Dieckmann Condensation

intermediate structure

HCl

AcOH

Reflux, 83% (2 steps)

intermediate structure

PhSOCH2Cl, i-Pr2NLi

THF

-78 °C

intermediate structure

KOH

H2O, THF

RT, 24 h, 95% (2 steps)

intermediate structure

n-Bu3PO, LiClO4

PhMe

Reflux, 60 min, 80%

intermediate structure

LiAlH4

Et2O

-20 °C, 91%

intermediate structure

+

intermediate structure

2,4,6-Trimethylbenzoic acid

125 °C, 3 h, 79%

See the Johnson-Claisen Rearrangement

intermediate structure

LiAlH4

Et2O

-20 °C

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C

See the Swern Oxidation

intermediate structure

(CH2OH)2, TsOH

PhH

Reflux, 60% (3 steps)

intermediate structure

9-BBN
NaOH , H2O2 , H2O

THF

35 °C, 60 min, 91%

intermediate structure

(PhSeO)2O

PhCl

120 °C, 15 min, 58%

intermediate structure

HCl

H2O, THF

RT, 24 h

intermediate structure

NH2OH.HCl

EtOH

Reflux, 40% (2 steps)

intermediate structure

H2, Pd/C

MeOH

69%

intermediate structure

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