Synthesis of Eurystatin A

Structure of Eurystatin A

C23H38N4O5

Principal investigatorJ. Edward Semple
Publication year2001
Synthesis typeTotal
Number of steps 9 (linear)
References
Tetrahedron Lett. 2001, 42, 6271.
Part 1 of 1
intermediate structure
CH3CO2CHO
Et3N
0 °C to RT, 90%
intermediate structure
N-Methylmorpholine, ClCO2CCl3
CH2Cl2
-40 to -15 °C, 98%
intermediate structure + intermediate structure + intermediate structure
CH2Cl2
0 °C to RT, 4 d, 80%
See the Passerini Reaction
intermediate structure
Et2NH
CH2Cl2
RT, ON, 75%
intermediate structure
Pd/C, H2
MeOH
95%
intermediate structure
NaHCO3, (PhO)2P(O)N3
DMF
0-4 °C, 5 d, 85%
intermediate structure
HCl
EtOAc
0 °C to RT, 100%
intermediate structure + intermediate structure
HOAt, EDC
DMF
RT, 93%
intermediate structure
Et3N, DMSO, Pyr.SO3
CH2Cl2
5 °C to RT, 75%
See the Parikh-Doering Oxidation
intermediate structure
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