Fragmentation of diastereoisomers (No ring fragmentation)

Background Colour:

This diastereoisomer cannot undergo ring expansion. This is because the starting material cannot place the mesylate group anti-periplanar to the ring-fusion bond (green bonds), so it cannot fragment.

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M. A. Drahl, M. Manpadi and L. J. Williams, Angew. Chemie - Int. Ed., 2013, 52, 11222–11251.