Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 12, Pages 8027-8034Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00879
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The first total synthesis of natural (-)-clavicipitic acid from gamma,gamma-dimethylallyltryptophan (DMAT), its biosynthetic precursor, is described. This is done by regio- and chemoselective, remote, nondirected C(sp(3))-H hydroxylation followed by aminocyclization. This study also features regio- and chemoselective Pd(0)-catalyzed linear prenylation at C4 of L-tryptophan boronic pinacol ester derivate, the latter obtained by a Lewis acid-promoted aziridine amino acid ring opening with 4-boronated indole. In addition, these results support the hypothesis that oxidative cyclization between amino acid nitrogen and the prenyl chain during clavicipitic acid biosynthesis can occur through the transient hydroxylated intermediate.
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