4.2 Article

SYNTHESIS OF 1,2,3,4,5,7-HEXAHYDRO-6H-AZOCINO[4,3-b]INDOL-6-ONES AS INTERMEDIATES FOR THE SYNTHESIS OF APPARICINE

Journal

HETEROCYCLES
Volume 82, Issue 1, Pages 349-370

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-10-S(E)5

Keywords

Indole; Mannich Reaction; Apparicine; Alkaloid; N-Phenylsulfonyl-2-pyrrolidone

Funding

  1. SERC
  2. EPSRC
  3. University of Manchester

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1-Phenylsulfonylindole is converted in eight steps into 2-(2-iodo-(Z)-but-2-en-1-y1)-6-methyl-1,2,3,4-tetrahydroazocino[4,3-b]indole, previously converted in one step into the indole alkaloid apparicine. The syntheses of other hexahydroazocino[4,3-b]indole potential precursors to the alkaloid are also described.

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