Synthesis of Hirsutene

C15H24
Principal investigator | Tarun K. Sarkar |
---|---|
Publication year | 1990 |
Synthesis type | Formal |
Number of steps | 16 (linear) |
References |
Part 1 of 1
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3,4-Dihydropyran,
TsOH
Et2O
Reflux, 5 h, 45%




TsOH
MeOH
Reflux, 90 min, 97%

NaOAc,
HCrO3Cl.Pyr
CH2Cl2
RT, 2 h, 87%



LiAlH4
Et2O
RT to Reflux, 5 h, 90%

H2Cr2O7.2Pyr
4 Å MS
AcOH, CH2Cl2
0 °C to RT, 50 min, 82%



HCrO3Cl.Pyr
CH2Cl2
RT, 90 min, 70%



H2,
Pt/C
1 atm
EtOAc
RT, 60 min, 98%

Remaining...
14% (5 step)
"See: J. Am. Chem. Soc. 1981, 103, 2744 and Tetrahedron Lett. 1976, 17, 195."
