Total Syntheses of Uvarindoles A and B, (±)-Pseudophrynaminol, and (±)-Pseudophrynamines 272A and 270 via Dearomative Indole Alkylation

Herein, we report the first total synthesis of alkaloid uvarindole B with an overall yield of 49% over five steps via double C3-alkylation of 5-bromoindole, Plancher rearrangement, and Negishi coupling as the key steps. We also disclose short total syntheses of uvarindole A, pseudophrynaminol, and pseudophrynamines 272A and 270 via dearomative indole alkylation.