Bispyrrolidinoindoline diketopiperazine alkaloids

The enantioselective total synthesis of the complex bioactive indole alkaloid enf-WIN 64821 was accomplished by L.E. Overman and co-workers." This natural product is a representative member of the family of the C2-symmetric bispyrrolidinoindoline diketopiperazine alkaloids. The stereospecific incorporation of two C-N bonds was achieved using the Mitsunobu reaction to convert two secondary alcohol functionalities to the corresponding alkyl azides with inversion of configuration. The azides subsequently were reduced to the primary amines and cyclized to the desired ib/s-amidine functionality. 

The bispyrrolidinoindoline diketopiperazine alkaloids ent-WIN 64821 (644) (Scheme 10.4) and ditryptophenaline (651) (Scheme 10.5) were prepared through total syntheses in 2001 by Overman et al. 414). The synthesis started with the... 

These two syntheses were the first examples of the concise preparation of C2-symmetric bispyrrolidinoindoline diketopiperazines with a cw-configuration of the two hydrogen atoms between the pyrrolidine nitrogens. The versatility of the route allows an efficient structural variation that might afford synthetic alkaloids with new or better biological profiles. 

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See also in sourсe #XX -- [ ]

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