Tetrahedron Letters p. 8105 - 8108 (1997)
Update date:2022-09-26
Topics:
Clissold, Cole
Kelly, Clare L.
Lawrie, Kenneth W.M.
Willis, Christine L.
A versatile route for the synthesis of 6-lactones via oxidation of tetrasubstituted cyclopentanenes is described. Each step in the synthetic pathway from cis-2-oxabicyclo[3.3.0]oct-6-en-2one to the ketones proceeds with excellent regio- and stereoselectivity and in good yield. Baeyer-Villiger oxidation of the cyclopentanone 21 with a further methyl substituent at C-1' of the side chain gives a single δ-lactone 22 whereas a 3:1 mixture of regioisomers 12 and 13 is obtained from the analogue 11 with no substituent at C-1'.
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