Synthesis of B-Araneosene

C20H32
Principal investigator | Elias J. Corey |
---|---|
Publication year | 2005 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1

Camphorsulfonic acid
H2O, MeCN
RT, 2 h

Camphorsulfonic acid
Acetone
RT, 3 h, 80% (2 steps)

MsCl,
Et3N
Pentane, PhH
0 °C, 1.5 h



LDA
THF
-90 to -78 °C, 8 h, 64%

NaOMe
MeOH
50 °C, 30 min, 96%




- H2O
- NaIO4
AcOH
RT to 55 °C, 3.5 h, 92%



LiAlH4
THF
Reflux, 10 min, 74%
"Also isolated was the C-2 epimer (20% yield)"


t-BuLi,
2-bromopropene
Et2O
-10 °C, 30 min, 82% (95% brsm)

i-Pr2NEt,
MeOCH2Cl,
n-Bu4N+ I-
THF
67 °C, 6 h, 92%

Li
NH3, THF
-60 °C, 3 h, 100%
