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Named reactions

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Tirandamycin B

Chemical structure of Tirandamycin_B
C22H27NO8
Author Philip DeShong
Publication year 1991
Synthesis type Total synthesis
Number of steps 18 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
CrCl3, LiAlH4
THF
0 °C to RT, 5 h, 30%

See the Nozaki-Hiyama-Kishi Reaction
Also isolated was the C2-epimer (47 % yield).
Chemical structure
TBSCl, Imidazole
DMF
RT, 5 d, 82%
Chemical structure
O3
CH2Cl2
-78 °C
Chemical structure
Zn, AcOH
Et2O, H2O
RT, 2 h, 95% (2 steps)
Chemical structure + Chemical structure
t-BuLi, (CH2NMe2)2
Et2O
-78 to 0 °C, 4 h, 42%

Also isolated was the C1-epimer (42 % yield).
Chemical structure
mCPBA
CH2Cl2
RT, 3 h, 89%

See the Achmatowicz Reaction
Chemical structure
HF, H2SiF6
MeCN, H2O
RT, 20 min, 35%
Chemical structure
NaBH4, CeCl3
MeOH
RT, 5 min, 99%

See the Luche Reduction
Chemical structure
mCPBA, Na3PO4
CH2Cl2, H2O
RT, 24 h, 73%

See the Prilezhaev Reaction
Chemical structure
Li.DTBBP
THF
-78 °C, 3 h, 95%
Chemical structure
H2Cr2O7.2Pyr
CH2Cl2
RT, 7 h, 85%
Chemical structure + Chemical structure
CrCl3, LiAlH4
THF
0 °C to RT, 3 h, 81%

See the Nozaki-Hiyama-Kishi Reaction
Chemical structure
OsO4, NaIO4
Dioxane , t-BuOH, H2O
RT, 7 h, 85%

See the Lemieux-Johnson Oxidation
Chemical structure
TsOH
PhH
Reflux, 2 h, 75%

Selectivity : 78:22 dr
Chemical structure + Chemical structure
KOt-Bu
THF
0 °C, 18 h, 72%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
CF3CO2H
RT, 5 min, 98%
Chemical structure
n-Bu4N+ F-
THF
RT, 21 h
Chemical structure
PhMe
Reflux, 91% (2 steps)
Chemical structure

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