4.6 Article

Concise total synthesis of (±)-aspidospermidine

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 18, Pages 5255-5259

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob00228a

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Funding

  1. NSFC [21125207, 21372103]
  2. MOST [2010CB833200]
  3. SRFDP [20130211110018]

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(+/-)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the synthesis of other Aspidosperma alkaloids.

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