Experimental study demonstrates a concise four-step total synthesis of tryprostatins A and B from gramine, indicating a streamlined route to prenylated indole alkaloids.
High Resolution Image Download MS PowerPoint Slide A concise four-step total synthesis of tryprostatins A and B has been developed, starting from commercially available gramine. The key step features a coupling between a C 2,N′ -diprenylated gramine salt and a diketopiperazine mediated by quinine as a bifunctional base. The synthesis afforded tryprostatins A and B along with their respective epimers in 1:1 ratios as determined by isolation and separation via column chromatography. The overall combined yields were 22% for tryprostatin A and its epimer and 44% for tryprostatin B and its epimer.
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Seideman et al. (2025) studied this question.
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