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Named reactions

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Daphnilactone A

Chemical structure of Daphnilactone_A
C23H35NO2
Author Clayton H. Heathcock
Publication year 1989
Synthesis type Total synthesis
Number of steps 12 (2 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
Br2, P (Red)
50 °C, 12.5 h, 82%

See the Hell-Volhard-Zelinsky Reaction
Chemical structure

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Part 2 of 2
Chemical structure
+
Chemical structure
i-Pr2NLi
THF
-78 to 0 °C, 4 h, 85%
Chemical structure
LiAlH4
Et2O
0 °C to RT, 60 min, 96%
Chemical structure + Chemical structure
Pyr
CH2Cl2
0 °C, 10 min, 95%
Chemical structure
ZnCl2, Na.Naphthalene
THF, HMPA
0 °C to RT, 9 h, 89%

See the Reformatsky Reaction
Chemical structure
LiAlH4
Et2O
RT, 6 h, 90%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min

See the Swern Oxidation
Chemical structure
NH3
CH2Cl2
0 °C to RT, 60 min, 47% (2 steps)

See the Diels-Alder Reaction
See the Ene Reaction
Chemical structure
H2, PtO2
1 atm
EtOH
RT, 60 min, 99%
Chemical structure
i-Bu2AlH
PhMe
Reflux, 72 h, 71%

See the Grob Fragmentation
Chemical structure
CrO3, H2SO4, Celite ®
Acetone, H2O
0 °C, 30 min

See the Jones Oxidation
Chemical structure
CH2O
Buffer (pH = 7)
RT, 60 min, 50% (2 steps)

See the Prins Reaction
Chemical structure

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