TOTAL SYNTHESIS OF HAMACANTHIN B CLASS MARINE BISINDOLE ALKALOIDS

Authors

  • Никита Е. Голанцов RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Алексей А. Феста RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Александра С. Голубенкова RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Хунг М. Нгуен RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Евгения А. Яковенко Ufa State Petroleum Technological University, 1 Kosmonavtov St., Ufa 450062, Russia
  • Алексей В. Варламов RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Леонид Г. Воскресенский RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia

DOI:

https://doi.org/10.1007/5599

Keywords:

bisindole alkaloids, 6'-debromohamacanthin B, 6''-debromohamacanthin B, diamines, 6', 6''-didebromohamacanthin B, hamacanthins, nitro compounds, reduction.

Abstract

A method for the synthesis of 1-(1H-indol-3-yl)ethane-1,2-diamines, key synthetic precursors of a number of marine alkaloids, has been developed based on the reduction of adducts of O-benzylhydroxylamine and N-protected 3-(2-nitrovinyl)indoles. For the first time, the total synthesis of 6',6''-didebromohamacanthin B, 6'-debromohamacanthin B, and 6''-debromohamacanthin B, the secondary metabolites of the sponges Spongosorites and Discodermia calyx, was carried out.

Author Biography

Никита Е. Голанцов, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia

Associate Professor, department of organic chemistry

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Published

2020-04-01

Issue

Vol. 56 No. 3 (2020)

Section

Original Papers