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Total Synthesis of (−)-Mersicarpine

“…10 It is known that a diazo coupling reaction is effective in installing a nitrogen atom at the 3-position of indoles. 11 Thus, reaction of 14 with benzenediazonium chloride proceeded cleanly to furnish 15. Subsequent lactam formation by treatment with sodium hydride followed by mesylation of the primary alcohol afforded 16.…”

“…Sonogashira coupling of 13 with 2-iodoaniline proceeded uneventfully to give alkynylaniline, which was cyclized with a gold(III) catalyst to afford indole 14 in good yield . It is known that a diazo coupling reaction is effective in installing a nitrogen atom at the 3-position of indoles . Thus, reaction of 14 with benzenediazonium chloride proceeded cleanly to furnish 15 .…”