Synthesis of Virantmycin

Structure of Virantmycin

C19H26ClNO3

Principal investigatorRalph A. Raphael
Publication year1990
Synthesis typeTotal
Number of steps 14 (linear)
References
Tetrahedron 1990, 46, 4587.
Part 1 of 1
intermediate structure + intermediate structure
NaH
THF
RT to 45 °C, 21.5 h, 91%
intermediate structure
Na
Propylene glycol
85 °C, 30 min, 65%
intermediate structure
LiCCH.(CH2NH2)2, C2H2
PhH, THF
35 to 50 °C, 68%
"The yield was 83 % brsm."
intermediate structure + intermediate structure
Pd(PPh3)2Cl2, CuI
Et2NH
RT, 16 h, 94%
See the Sonogashira Coupling
intermediate structure
MsOH
H2O, THF
40 °C, 20 h, 63%
See the Meyer-Schuster Rearrangement
intermediate structure
NaBH4
MeOH
RT
intermediate structure
Ph3P
CCl4
54 °C, 5 h, 76% (2 steps)
intermediate structure
HCO2Ac
HCO2H
RT, 12 h, 90%
intermediate structure
NaHCO3, mCPBA
CH2Cl2
RT, 72 h, 86%
See the Prilezhaev Reaction
intermediate structure
Pd/C, H2
1 atm
Dioxane
RT, 21 h, 64%
intermediate structure
WCl6, n-BuLi
THF
-78 °C to RT, 90 min, 45%
intermediate structure
NaOH
MeOH
RT, 20 h, 80%
intermediate structure
SOCl2
CH2Cl2
40 °C, 5.5 h, 45%
intermediate structure
LiOH
H2O, MeCN
70 °C, 4 h, 73%
intermediate structure
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