4.5 Article

Towards the total synthesis of keramaphidin B

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 12, Issue -, Pages 1096-1100

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.12.104

Keywords

bifunctional organocatalyst; enantioselective Michael addition; keramaphidin B; nitro-Mannich lactamisation cascade

Funding

  1. EPSRC [EP/M50659X/1]
  2. EPSRC [EP/G007802/1] Funding Source: UKRI
  3. Engineering and Physical Sciences Research Council [1112321, EP/G007802/1] Funding Source: researchfish

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The enantio-and diastereoselective Michael addition of a delta-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.

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