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A Concise Total Synthesis of Tryprostatins A and B and Epimers
Sophia Seideman1, Khorshada Jahan1, Frank Holger Foersterling1
1Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 2000 E Kenwood Blvd., Milwaukee, Wisconsin 53211-3029, United States.
None:
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 C2,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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