Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorTarun K. Sarkar
Publication year1990
Synthesis typeFormal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure
3,4-Dihydropyran, TsOH
Et2O
Reflux, 5 h, 45%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-60 °C to RT, 50 min, 80%
See the Swern Oxidation
intermediate structure + intermediate structure
TMS2NNa
THF
-78 °C to RT, ON, 61%
See the Wittig Reaction
intermediate structure
TsOH
MeOH
Reflux, 90 min, 97%
intermediate structure
NaOAc, HCrO3Cl.Pyr
CH2Cl2
RT, 2 h, 87%
intermediate structure
NaH, (EtO)2P(O)CH2CO2Et
DME
RT, 3 h, 76%
intermediate structure
PhMe
245 °C, 30 h, 97%
See the Ene Reaction
intermediate structure
LiAlH4
Et2O
RT to Reflux, 5 h, 90%
intermediate structure
H2Cr2O7.2Pyr
AcOH, CH2Cl2
0 °C to RT, 50 min, 82%
intermediate structure
DMSO, NaH, TMSI
THF
0 °C to RT, 2 h, 61%
intermediate structure
TiCl4
CH2Cl2
-78 °C, 60 min, 72%
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 90 min, 70%
intermediate structure
O2, CuCl2, PdCl2
DMF, H2O
RT to 57 °C, 4.5 h, 77%
intermediate structure
KOH
EtOH, H2O
55 °C, 90 min, 40%
intermediate structure
H2, Pt/C
EtOAc
RT, 60 min, 98%
intermediate structure
Remaining...
14% (5 step)
"See: J. Am. Chem. Soc. 1981, 103, 2744 and Tetrahedron Lett. 1976, 17, 195."
intermediate structure