Synthesis of Curvularin

Structure of Curvularin

C16H20O5

Principal investigatorBrian M. Stoltz
Publication year2010
Synthesis typeTotal
Number of steps 14 (3 parts)
References
Part 1 of 3
intermediate structure
Imidazole, TIPSCl
DMF
RT, 36 h, 41%
intermediate structure
BnBr, Cs2CO3
MeCN
RT
intermediate structure
n-Bu4N+ F-
THF
RT, , 42% (2 steps)
intermediate structure
NBS
CH2Cl2
-78 °C, , 90%
intermediate structure
TMS2NH
THF
70 °C, 5 h
intermediate structure
  1. n-BuLi
  2. Tf2O
-100 to -80 °C, 30 min, 74% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
  1. i-Pr2NLi
  2. Acrolein
THF
-78 °C, 40 min, 76%
See the Aldol Addition
intermediate structure
TMSCl, TMS2NH
THF
70 °C, 5 h
intermediate structure
Grubbs-Hoveyda catalyst (3rd gen.)
PhH
Reflux, 20 h
intermediate structure
HCl
H2O, THF
RT, 2 h, 57% (2 steps)
intermediate structure
H2, Pd/C
1 atm
EtOH
RT
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 93% (2 steps)
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
CsF
MeCN
40 °C, , 30%
intermediate structure
H2, Pd/C
1 atm
MeOH, THF
RT, , 60%
intermediate structure