Synarchive logo
Google+ Facebook Twitter RSS Feed
Support this website
Synarchive is free but requires a lot of work. If you enjoy and find it useful, please support us by making a donation.
Named reactions

Get references and more from over 229 named organic chemical reaction

Go to the named reaction index

Protecting Groups

Get the conditions needed to install/remove a wide range of protecting groups.

Go to the protecting groups index

Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author R. Daniel Little
Publication year 1983
Synthesis type Formal synthesis
Number of steps 16 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
NaBH4
THF
0 °C to RT, 3.5 h, 61%
Chemical structure
i-Bu2AlH
Et2O
-20 °C, 90 min, 76%
Chemical structure
Ph3P=CH2
See the Wittig Reaction
No yield reported.
Chemical structure
HCrO3Cl.Pyr, Celite ®
CH2Cl2

No yield reported.
Chemical structure + Chemical structure
Et2NH
MeOH
5 °C to RT, 2 h, 77%
Chemical structure + Chemical structure
Et2O
0 °C, 60 min, 100%

See the Diels-Alder Reaction
Chemical structure
Reagent structure
AcOH
CH2Cl2

No yield reported.
Chemical structure
K3Fe(CN)6, LiClO4
-1.76 V vs Ag/AgCl
DMF, H2O
0 °C to RT, 2 h, 55%
Chemical structure
THF
Reflux, 6 h, 63%

Also isolated was the C6-epimer (13 % yield).
Chemical structure
BH3.THF
THF
Chemical structure
HCrO3Cl.Pyr, Celite ®
CH2Cl2
61% (2 steps)
Chemical structure
HCO2Et, NaOMe
PhH
0 °C to RT, 20 h, 97%

See the Claisen Condensation
Chemical structure
n-BuSH, TsOH, MgSO4
PhH
Reflux, 20 h, 82%
Chemical structure
MeI, KOt-Bu
t-BuOH
0 °C to reflux, 30 min, 50%

The yield was 59% BRSM.
Chemical structure
KOH
H2O, Ethylene Glycol
Reflux, 24 h, 51%
Chemical structure

Report an error in this part

Remaining...
70% (1 step)

See: Tetrahedron Lett. 1976, 17, 195.
comments powered by Disqus
homepage - authors - molecules - named reactions - protecting groups - advanced search - contact
© 2011-2017 SynArchive