4.4 Article

Synthesis of (+)-9a-epi-Stemoamide via DBU-Catalyzed Michael Addition of Nitroalkane

Journal

SYNLETT
Volume -, Issue 13, Pages 2188-2190

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1217558

Keywords

Michael addition; nitroalkane; stemoamide; synthesis; unsaturated butyrolactone

Funding

  1. NSFC [90713007, 20772141, 20625204, 20632030]
  2. MOST_863 [2006AA09Z405, 2006AA09Z446]

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We describe a practical synthesis of (+)-9a-epi-stemoamide, which has been achieved in six steps from a,p-unsaturated gamma-butyrolactone. The main features of the current approach include a DBU-catalyzed Michael addition of nitroalkane and a reductive lactamization of nitro esters.

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