Opening of aryl-substituted epoxides to form quaternary stereogenic centers: synthesis of (-)-mesembrine.

Abstract

[reaction: see text] Cycloalkanones are easily converted into aryl-substituted cyclic alkenes by the addition of an aryl Grignard reagent followed by dehydration. These alkenes are good substrates for asymmetric epoxidation. We have found that the addition of allylic and benzylic Grignard reagents can occur preferentially at the benzylic position of the derived epoxides to give the quaternary stereogenic center. This approach led to a short synthesis of the nanomolar serotonin re-uptake inhibitor (-)-mesembrine.

• Authors: Douglass F Taber, Yigang He
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 70 Issue 19 Pg. 7711-4 (Sep 16 2005) ISSN: 0022-3263 [Print] United States
• PMID: 16149803 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Indole Alkaloids
• mesembrine

Topics

• Indole Alkaloids (chemical synthesis)
• Stereoisomerism