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A nine-step synthesis of pentacyclic key intermediate 11 of cribrostatin 4 (2) along with renieramycin I (1i) from 3,6-bisarylpiperazine-2,5-dione derivative 3 is described. The key step of this synthesis is the stereoselective cyclization of lactam nitrogen with diethoxyethyl benzoate, followed by the stereoselective hydrogenation to generate ABC ring system 6.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Synthesis of Renieramycins: Construction of the Core Ring System of Cribrostatin 4 through Modified Pictet-Spengler Cyclization of 3,6-Bisarylpiperazine-2,5-dione with Diethoxyethyl Benzoate