Synthesis of Daphnilactone A

Structure of Daphnilactone A

C23H35NO2

Principal investigatorClayton H. Heathcock
Publication year1989
Synthesis typeTotal
Number of steps 12 (2 parts)
References
Part 1 of 2
intermediate structure
Br2, P (Red)
50 °C, 12.5 h, 82%
intermediate structure
Part 2 of 2
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 to 0 °C, 4 h, 85%
intermediate structure
LiAlH4
Et2O
0 °C to RT, 60 min, 96%
intermediate structure + intermediate structure
Pyr
CH2Cl2
0 °C, 10 min, 95%
intermediate structure
ZnCl2, Na.Naphthalene
THF, HMPA
0 °C to RT, 9 h, 89%
intermediate structure
LiAlH4
Et2O
RT, 6 h, 90%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min
See the Swern Oxidation
intermediate structure
NH3
CH2Cl2
0 °C to RT, 60 min, 47% (2 steps)
See the Ene Reaction
intermediate structure
H2, PtO2
EtOH
RT, 60 min, 99%
intermediate structure
i-Bu2AlH
PhMe
Reflux, 72 h, 71%
intermediate structure
CrO3, H2SO4, Celite
Acetone, H2O
0 °C, 30 min
See the Jones Oxidation
intermediate structure
CH2O
Buffer (pH = 7)
RT, 60 min, 50% (2 steps)
See the Prins Reaction
intermediate structure