106542-22-7Relevant academic research and scientific papers
CLAISEN-REARRANGEMENT-MEDIATED RING CONTRACTION OF MACROCYCLIC LACTONES A NEW APPROACH TO CARBOCYCLES AND HETEROCYCLES
Funk, Raymond L.,Abelman, Matthew, M.,Munger, John D.
, p. 2831 - 2846 (2007/10/02)
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.
A New Approach to Heterocycles: Synthesis of (+/-)-N-Benzoylmeroquinene Methyl Ester
Funk, Raymond L.,Munger, John D.
, p. 4319 - 4320 (2007/10/02)
A new approach to the total synthesis of N-benzoylmeroquinene methyl ester is described and features the stereospecific Claisen rearrangement of the (E)-silyl ketene acetal derived from azalactone 7 as the key step in the construction of the disubstituted
