Synthesis of Aplysin

Structure of Aplysin

C15H19BrO

Principal investigatorDavid C. Harrowven
Publication year1999
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure
ZrCl4
CH2Cl2
RT, 24 h, 93%
intermediate structure
Me2SO4, KOH
Acetone
RT, 15 h, 97%
intermediate structure
Morpholine, S8
100 °C, 24 h, 76%
intermediate structure
MeI
THF, H2O
Reflux, 18 h, 90%
intermediate structure
t-BuLi, 4-Iodobutene
THF
-78 to 0 °C, 5 h, 48%
intermediate structure
BCl3
CH2Cl2
0 °C to RT, 2 h, 81%
intermediate structure
  1. i-PrN(Cy)Li
  2. MeI
THF
-78 to 0 °C, 4 h, 84%
intermediate structure
Cp2TiCl2, AlMe3
PhMe
-78 to 0 °C, 6 h, 66%
intermediate structure
(t-BuS)2
Hexane(s)
RT, 24 h, 54%
"Also isolated was the C3-epimer (7 % yield)."
intermediate structure
Ni (Raney)
EtOH
Reflux, 20 h, 74%
intermediate structure
Br2, Na2CO3
Petroleum ether
RT, 2 min, 75%
intermediate structure