An efficient formal synthesis of the sesquiterpenoid longifolene.
Through a convenient ring expansion reaction of key intermediate 1, enone 5, containing the longifolene skeleton, was produced. Elaboration of 5 via hydrogenation, Wittig reaction, Simmons-Smith reaction, and subsequent hydrogenolysis led to ketone 9. Reductive debromination of 9 afforded 10, the penultimate precursor to longifolene. This formal total synthesis was accomplished in 13 steps using commercially available Wieland-Miescher ketone as the starting material.
Karimi
Sasan
S
Department of Chemistry, Queensborough Community College/CUNY, Bayside, New York 11364, USA. skarimi@qcc.cuny.edu
Tavares
Paula
P
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007202:Indicators and Reagents; D007659:Ketones; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D007202:Indicators and Reagents; D007659:Ketones; D012717:Sesquiterpenes; C035607:longifolene