Synthesis of Englerin A

Structure of Englerin A

C26H34O6

Principal investigatorWilliam J. Chain
Publication year2011
Synthesis typeTotal
Number of steps 9 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
LDA
THF
-78 °C to RT, 8.5 h, 89%
intermediate structure
DBU
THF
RT, 12 h, 72%
intermediate structure
Part 2 of 3
intermediate structure
Grubbs catalyst (2nd gen.)
CH2Cl2
Reflux, 48 h, 99%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
LDA
THF
-78 °C to RT, 2 h, 75%
"66:33 dr"
intermediate structure
SmI2
HMPA, THF
RT, 3 h, 43%
intermediate structure + intermediate structure
Special reagent
DMAP, Et3N
PhMe
RT, 2 d, 86%
intermediate structure
NaBH4
MeOH
0 °C, 30 min, 100%
intermediate structure
  1. TMS2NLi
  2. (imid)2SO2
-10 °C to RT, 12.5 h, 100%
intermediate structure
Special reagent
18-Crown-6
PhMe
Reflux, 36 h, 74%
intermediate structure