A Concise Total Synthesis of Tryprostatins A and B and Epimers
Sophia Seideman, Khorshada Jahan, Frank Holger Foersterling, M. Mahmun Hossain
TL;DR
Scientists developed a short and efficient method to synthesize two natural compounds, tryprostatins A and B, along with their mirror-image versions.
Contribution
A four-step synthesis of tryprostatins A and B using quinine as a bifunctional base is introduced.
Findings
The synthesis starts from commercially available gramine and includes a key coupling step mediated by quinine.
The method produces tryprostatins A and B and their epimers in 1:1 ratios with overall yields of 22% and 44%.
The epimers were isolated and separated using column chromatography.
Abstract
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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Taxonomy
TopicsMicrobial Natural Products and Biosynthesis · Synthetic Organic Chemistry Methods · Carbohydrate Chemistry and Synthesis