Claisen-rearrangement-mediated ring contraction of macrocyclic lactones
1986; Elsevier BV; Volume: 42; Issue: 11 Linguagem: Inglês
10.1016/s0040-4020(01)90572-1
ISSN1464-5416
AutoresRaymond L. Funk, Matthew M. Abelman, J. D. JUN. MUNGER,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoMacrocyclic ketene acetals 3 undergo Claisen rearrangements smoothly and constitute a viable and general approach to hetero- or carbocyclic ring systems 4. This novel ring contraction process is subject to high internal asymmetric induction (cf. lactones 7 → carbocycles 8) as well as relative asymmetric induction in the rearrangements of ketene acetals derived from lactones 18, 23 and 27. Finally, N-benzoylmeroquinene methyl ester (37) was prepared to demonstrate the potential of this methodology in heterocycle synthesis.
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