Synthesis of renieramycins: construction of the core ring system of cribrostatin 4 through modified Pictet-Spengler cyclization of 3,6-bisarylpiperazine-2,5-dione with diethoxyethyl benzoate

Chem Pharm Bull (Tokyo). 2011;59(6):787-92. doi: 10.1248/cpb.59.787.

Abstract

A nine-step synthesis of pentacyclic key intermediate 11 of cribrostatin 4 (2) along with renieramycin I (1i) from 3,6-bisarylpiperazine-2,5-dione derivative 3 is described. The key step of this synthesis is the stereoselective cyclization of lactam nitrogen with diethoxyethyl benzoate, followed by the stereoselective hydrogenation to generate ABC ring system 6.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoates / chemistry*
  • Cyclization
  • Hydrogenation
  • Isoquinolines / chemistry*
  • Molecular Conformation
  • Piperazines / chemistry*
  • Tetrahydroisoquinolines / chemical synthesis*
  • Tetrahydroisoquinolines / chemistry

Substances

  • Benzoates
  • Isoquinolines
  • Piperazines
  • Tetrahydroisoquinolines
  • cribrostatin 4
  • renieramycin I
  • 3,6-bis(5-chloro-2-piperidyl)-2,5-piperazinedione