Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 4, Pages 571-576Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700511
Keywords
alpha-ambrinol; asymmetric epoxidation; catalysis; titanium; total synthesis
Categories
Ask authors/readers for more resources
We describe the first enantioselective synthesis of the odorant compound (-)-alpha-ambrinol (96% ee) from commercial geranylacetone. The key steps are a Jacobsen's asymmetric epoxidation and a titanium-catalyzed stereoselective cyclization initiated by radical epoxide opening. ne oxirane ring opening proceeds with retention of configuration at the epoxide chiral center, giving a secondary alcohol which can be advantageously exploited to raise the ee provided by the synthetic sequence. We also synthesized (+)-alpha-ambrinol by a closely related procedure, showing the synthetic versatility of combining titanium-catalyzed cyclization with Jacobsen's epoxidation reactions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available