Synthesis of Isodityrosine

Structure of Isodityrosine

C18H20N2O6

Principal investigator	Michael E. Jung
Publication year	1999
Synthesis type	Total
Number of steps	14 (3 parts)
References	J. Org. Chem. 1999, 64, 2976.

Part 1 of 3

intermediate structure

Et3N, Boc2O

Dioxane , H2O

0 °C to RT, 18.5 h, 92%

intermediate structure

CHCl3, NaOH

H2O

Reflux, 4 h, 33% (49% BRSM)

See the Reimer-Tiemann Formylation

intermediate structure

K2CO3, BnBr

CHCl3, MeOH

Reflux, 4 h, 71%

See the Williamson Ether Synthesis

intermediate structure

(PhSe)2, H2O2

CH2Cl2, H2O

RT, 18 h

See the Dakin Oxidation

intermediate structure

NH3

MeOH

RT, 80 min, 78% (2 steps)

intermediate structure

BnBr, NaHCO3

DMF

RT, 18 h, 76%

intermediate structure

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Part 2 of 3

intermediate structure

SOCl2

MeOH

-10 °C to Reflux, 3 h

intermediate structure

Et3N, Boc2O

Dioxane , H2O

0 °C to RT, 18 h, 91% (2 steps)

intermediate structure

KOAc, (dppf)PdCl2, B2Pin2

DMSO

80 °C, 20 h, 81%

See the Miyaura Borylation

intermediate structure

HN(CH2CH2OH)2

EtOH, i-PrOH

RT, 72 h, 58%

intermediate structure

HCl

H2O, THF

RT, 30 min, 89%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

Pyr, Cu(OAc)2

4 A MS

CH2Cl2

RT, 18 h, 60%

See the Chan-Evans-Lam Coupling

intermediate structure

H2, Pd/C

1 atm

THF

RT, 18 h

intermediate structure

HCl

H2O

65 °C, 6 h, 92% (2 steps)

intermediate structure

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