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Synthesis and enantioseparation of (±)- marinoaziridine precursors

Aziridines are an important class of molecules present as the key structural component in a number of biologically active natural products [1]. Apart from their pharmacological purposes, aziridines are also valuable from a synthetic point of view as they can function as building blocks for the synthesis of numerous biologically active and natural compounds [2]. Our interest was primarly focused on the construction of epoxides 1a-1c and 2a-2c as important precursors in the total synthesis of marinoaziridines A, B and their derivatives (Figure 1). Marinoaziridines A and B are the first aziridine-based alkaloids isolated from Gram-negative bacteria from marine sediment [3]. In conducted research the (±)-marinoaziridine precursors 1a-1c and 2a-2c were prepared by the addition of the achiral sulfur ylide derived from sulfonium salt I or II to a carbon-oxygen double bond of the corresponding aldehydes Ia-Ic in good yield.

epoksid ; , 2-kinolinoni ; kiralna nepokretna faza

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