4.8 Article

A Five-Step Synthesis of (S)-Macrostomine from (S)-Nicotine

Journal

ORGANIC LETTERS
Volume 12, Issue 20, Pages 4513-4515

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol101887b

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Funding

  1. North Carolina Biotechnology Center
  2. National Science Foundation [CHE-0078253]
  3. Taracept Inc
  4. NCSU for a North Carolina State University

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A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridine Die Is Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product

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