4.8 Article

Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials

Journal

ORGANIC LETTERS
Volume 22, Issue 21, Pages 8387-8391

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03020

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Funding

  1. Swedish Research Council Formas
  2. Operational Programme Research, Development and Education, project name: Improvement of internationalization in the field of research and development at Charles University, through the support of quality projects MSCA-IF [CZ.02.2.69/0.0/0.0/17_050/0008466]

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Here we present a polycyclization of oxotriphenylhex-anoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is compatible with an array of functional groups, allowing pharmacophoric elements to be introduced post cyclization.

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