Tetrahedron Letters p. 7329 - 7332 (1989)
Update date:2022-07-31
Topics:
Kende
Kaldor
The tricyclic α-sulfonyl lactone 4 is converted by alkoxides to bicyclic acids 5,6; the homologous α-sulfonyl lactone 8 yields bicyclic acid 10 or the cyclononene ketoacid 9. These products arise from a common Grob fragmentation mechanism (Scheme 3), in which the fate of the medium-ring trans-cycloalkene intermediates 12 is determined by ring size and by the nature of the nucleophilic base used.
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(1971)