CLAISEN-REARRANGEMENT-MEDIATED RING CONTRACTION OF MACROCYCLIC LACTONES A NEW APPROACH TO CARBOCYCLES AND HETEROCYCLES
Macrocyclic 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.
Funk, Raymond L.,Abelman, Matthew, M.,Munger, John D.
p. 2831 - 2846
(2007/10/02)
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