Synthesis of Epolactaene

Structure of Epolactaene

C21H27NO6

Principal investigatorYujiro Hayashi
Publication year2002
Synthesis typeTotal
Number of steps 20 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
PhH
90 °C, 90 min, 98%
See the Wittig Reaction
intermediate structure
TBSCl, Imidazole
CH2Cl2, DMF
RT, 20 min, 99%
intermediate structure
i-Bu2AlH
CH2Cl2
0 °C, 60 min
intermediate structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 90 min, 94% (2 steps)
intermediate structure + intermediate structure
NaH
THF
0 °C to RT, 60 min, 96%
intermediate structure
  1. i-Pr2NLi
  2. MeCHO
THF, HMPA
-78 °C, 4.5 h, 96%
See the Aldol Addition
intermediate structure
MsCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 90 min
intermediate structure
DABCO
MeOH
100 °C, 5 d, 86% (2 steps)
intermediate structure
n-Bu4N+ F-
THF
0 °C, 3 h, 100%
intermediate structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 90 min, 100%
intermediate structure + intermediate structure
n-BuLi
DME
0 °C to RT, 40 min, 100%
intermediate structure
n-BuLi, MeCN
THF
-88 to -78 °C, 60 min, 93%
intermediate structure
CF3CO2H
CH2Cl2
0 °C to RT, 20 min
intermediate structure
CH2N2
Et2O
-78 °C, , 92% (2 steps)
intermediate structure + intermediate structure
(CH2NH2)2.2AcOH
PhH
RT, 2 h
intermediate structure
Ph3COOH, n-BuLi
THF
-78 °C, 2 h
intermediate structure
NH4F, AcOH
THF, H2O
RT, 90 min
intermediate structure
SiO2
EtOAc, Hexane(s)
intermediate structure
NH3
MeOH, H2O
0 °C, 30 min, 22% (5 steps)
intermediate structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 2 h, 78%
intermediate structure