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Named reactions

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Search synthesis

Phyllanthocin

Chemical structure of Phyllanthocin
C25H30O7
Author David R. Williams
Publication year 1984
Synthesis type Total synthesis
Number of steps 30 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Me2CuLi
Et2O
-78 °C
Chemical structure
3,4-Dihydropyran, TsOH
Chemical structure
LiAlH4
Et2O
RT, 18 h
Chemical structure
TsOH
MsOH
RT, 70% (4 steps)
Chemical structure
TsOH
Acetone
67%

Also isolated was the 6-membered acetonide (13 % yield).
Chemical structure
TBDPSCl, DMAP
CH2Cl2
RT, 2 h, 98%
Chemical structure
(CH2SH)2, TsOH
CHCl3
Reflux, 60 min
Chemical structure
TsCl, Et3N
CH2Cl2
36 h
Chemical structure
NaH
THF
0 °C to RT, 76% (3 steps)
Chemical structure + Chemical structure
n-BuLi
THF
-78 to 0 °C, 6.5 h

See the Corey-Seebach Reaction
Chemical structure
MeO(CH2)2OCH2Cl, i-Pr2NEt, DMAP
CH2Cl2
0 °C, 2 h, 95% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
mCPBA
CH2Cl2
10 °C to RT, 89%

See the Prilezhaev Reaction
Mixture of isomers.
Chemical structure
n-BuLi, 2,6-Dimethylpiperidine
Carius tube
Et2O
0 °C to 50 °C, 75 min, 90%

Mixture of isomers.
Chemical structure
TBSCl, Imidazole
DMF
RT, 9 h, 34%

Also isolated was the C5-epimer (45 % yield).
Chemical structure
BH3.THF, H2O2
THF
0 °C to RT, 2 h, 46%

Also isolated was the C2-epimer (19 % yield).
Chemical structure + Chemical structure
<50%

The experimental procedure for this resolution was unavailable in the article.
Chemical structure
KOH
MeOH, H2O

The experimental procedure for this resolution was unavailable in the article.
Chemical structure
HCrO3Cl.Pyr
CH2Cl2
RT, 90%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
t-BuLi, HMPA
THF
-78 to -20 °C, 2 h, 81%

Selectivity : 78:12 dr
See the Corey-Seebach Reaction
Chemical structure
n-Bu4N+ F-
THF
RT, 2 h, 51-61%

The epimers were carried on separately.
Chemical structure
HgCl, HgO
MeCN, H2O
RT, 30 min, 42%

The epimers were carried on separately. Also isolated were 2 isomeric spiroketals (38 % yield, see next step).
Chemical structure
CF3CO2H
CH2Cl2
0 °C, 1 min, 83%

Also isolated was the desired CX-epimer (13% yield, see next step).
Chemical structure
CF3CO2H, MeMgCl
CH2Cl2
RT, 6 h, 63%
Chemical structure
CrO3, H2SO4
Acetone
RT, 45 min, 75%

See the Jones Oxidation
Chemical structure
H2, Pd/C
EtOAc
RT, 45 min, 82%
Chemical structure
CrO3, H2SO4
Acetone
RT, 30 min, 95%

See the Jones Oxidation
Chemical structure
CH2N2
Et2O
RT, 1 min, 100%
Chemical structure
ZnBr2
CH2Cl2
RT, 2 h, 100%
Chemical structure
Me3S+ I-, NaH
DMSO
RT, 30 min, 92%

Selectivity : 97:03 dr
See the Johnson-Corey-Chaykovsky Reaction
Chemical structure + Chemical structure
DMAP
CH2Cl2
RT to 40 °C, 8 h, 73%
Chemical structure

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