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<p>The development of efficient sequences for the total synthesis of 20-deethyldascarpidone is described. The central step in these syntheses is the intramolecular aldol reaction, which constructs the tetracyclic 1,5-methanoazocino[4,3-<i>b</i>]indole ring system in five steps from 2,3-dihydrospiro[carbazole-1,2′-[1,3]dithiolan]-4(9<i>H</i>)-one (<b>1</b>) and <i>N</i>-methylglycine (<b>2</b>). Using one additional step, this intermediate is advanced to 20-deethyldascarpidone over five steps with 49% overall yield, forming the constituent ABCD-ring system of Strychnos alkaloids for the first time in a different way.</p>

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A New Synthetic Strategy for Deethyldasycarpidone Based on an Azocino[4,3-b]indole Intermediate

  • 期刊论文

  • 发表日期：

    2026年3月1日

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  • Nesimi Uludag,
  • Omer Karabudak

摘要

The development of efficient sequences for the total synthesis of 20-deethyldascarpidone is described. The central step in these syntheses is the intramolecular aldol reaction, which constructs the tetracyclic 1,5-methanoazocino[4,3-b]indole ring system in five steps from 2,3-dihydrospiro[carbazole-1,2′-[1,3]dithiolan]-4(9H)-one (1) and N-methylglycine (2). Using one additional step, this intermediate is advanced to 20-deethyldascarpidone over five steps with 49% overall yield, forming the constituent ABCD-ring system of Strychnos alkaloids for the first time in a different way.