A claisen rearrangement strategy for the three-atom ring expansion of cyclic ketones. A total synthesis of (±) precapnelladiene
1990; Elsevier BV; Volume: 31; Issue: 47 Linguagem: Inglês
10.1016/s0040-4039(00)97175-2
ISSN1873-3581
AutoresNicos A. Petasis, Michael A. Patane,
Tópico(s)Chemical synthesis and alkaloids
ResumoThe aldol products derived from cyclic ketone enolates undergo Baeyer-Villiger oxidation to give after dehydration the corresponding vinylic-substituted lactones. Titanium-mediated olefination followed by Claisen rearrangement leads to an overall three-atom ring-expansion. The application of this strategy to a concise total synthesis of (±) precapnelladiene (22) is reported.
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