Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 18, Pages 6944-6951Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034703l
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Tryprostatin B was synthesized in 32% overall yield from the readily available dipeptide anhydride cyclo-(L-Trp-L-Pro). Its tandem C-3 prenylation/cyclization gave the corresponding pentacyclic pyrroloindole systems bearing a prenyl group at the indole C-3 position. These compounds were then submitted to acid-catalyzed opening of the newly formed ring, with concomitant migration of the prenyl group to the indole C-2 position. The alanine analogue of tryprostatin B was also prepared using a similar sequence. The successful implementation of this strategy strengthens the case for a biosynthetic route for the tryprostatins along similar lines.
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