Synthesis of Clavukerin A

Structure of Clavukerin A

C12H18

Principal investigatorHans J. Schäfer
Publication year2002
Synthesis typeFormal
Number of steps 7 (linear)
References
Tetrahedron Lett. 2002, 43, 2683.
Part 1 of 1
intermediate structure
AcOOH, Na2CO3
CH2Cl2
RT, 24 h, 68%
See the Prilezhaev Reaction
intermediate structure
CuCN, MeLi
Et2O
-78 °C, 81%
intermediate structure
CrO3, H2SO4
CH2Cl2, H2O
0 °C, 60 min, 68%
See the Jones Oxidation
intermediate structure + intermediate structure
TiCl4
CH2Cl2
-78 °C, 60 min, 46%
See the Danheiser Annulation
"Also isolated was the C8-epimer (46 % yield)."
intermediate structure
K2CO3
MeOH
RT, 2 h
intermediate structure
n-Bu4N+ F-
MeOH
78% (2 steps)
intermediate structure
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Remaining...
73% (2 steps)
"See : J. Org. Chem. 1991, 56, 6829."
intermediate structure