Synthesis of Elailoide

Structure of Elailoide

C42H68O12

Principal investigatorDavid A. Evans
Publication year1997
Synthesis typeTotal
Number of steps 22 (2 parts)
References
Part 1 of 2
intermediate structure
  1. i-Pr2NLi
  2. EtI
THF
-78 to 20 °C, 24 h, 82%
intermediate structure
2,6-Lutidine, TBSOTf
CH2Cl2
60 min, 0 °C, 98%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 to -40 °C, 90 min, 100%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 80 min, 100%
See the Swern Oxidation
intermediate structure + intermediate structure
BF3.OEt2
CH2Cl2
-78 °C, 45 min, 89%
intermediate structure
n-Bu4N+ F-
THF
RT, 10 min, 96%
intermediate structure
2,6-Lutidine, t-Bu2Si(OTf)2
CH2Cl2
0 °C, 60 min, 91%
intermediate structure
  1. Me2S
  2. O3
CH2Cl2, MeOH
-78 °C to RT, 3 h, 90%
intermediate structure
Part 2 of 2
intermediate structure + intermediate structure
Et3N, n-Bu2BOTf
CH2Cl2
-78 to 0 °C, 80 min, 86%
intermediate structure
2,6-Lutidine, TESOTf
CH2Cl2
0 °C, 30 min, 92%
intermediate structure
LiBH4
Et2O, H2O
RT, 3 h, 87%
intermediate structure
DMAP, Et3N, Ph3CCl
CH2Cl2
RT, 6 h, 92%
intermediate structure
  1. H2O
  2. H2O2
  3. 9-BBN
THF
0 °C, 3 h, 89%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 70 min, 98%
See the Swern Oxidation
intermediate structure + intermediate structure
TMS2NLi
THF
-78 °C, 12 h, 85%
intermediate structure
Pyr.HF
THF
0 °C, 4 h, 93%
intermediate structure
KOH
H2O, MeOH, THF
RT, , 98%
intermediate structure
DMAP, Et3N
PhMe
RT, 105 min, 62%
intermediate structure
Camphorsulfonic acid
MeOH, THF
RT, , 65%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, , 96%
See the Swern Oxidation
intermediate structure + intermediate structure
i-Pr2NEt, PhBCl2
CH2Cl2
-78 to 0 °C, 2.5 h, 66%
See the Aldol Addition
intermediate structure
Pyr, Pyr.HF
H2O, THF
RT, 3 h, 91%
intermediate structure