Tetrahedron p. 15813 - 15826 (1997)
Update date:2022-08-03
Topics:
Manny, Anthony J.
Kjelleberg, Staffan
Kumar, Naresh
De Nys, Rocky
Read, Roger W.
Steinberg, Peter
A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation. occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described.
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