Samarium(II) folding cascades involving hydrogen atom transfer for the synthesis of complex polycycles

Research output: Contribution to journalArticle

  • Authors:
  • Mateusz Plesniak
  • Monserrat Herenia Garduno Castro
  • Philipp Lenz
  • Xavier Just-Baringo
  • David Procter

Abstract

The expedient assembly of complex, natural product-like small molecules can deliver new chemical entities with the potential to interact with biological systems and inspire the development of new drugs and probes for biology. Diversity-oriented synthesis is a particularly attractive strategy for the delivery of complex molecules in which the 3-dimensional architecture varies across the collection. Here we describe a folding cascade approach to complex polycyclic systems bearing multiple stereocentres mediated by reductive single electron transfer (SET) from SmI2. Simple, linear substrates undergo three different folding pathways triggered by reductive SET. Two of the radical cascade pathways involve the activation and functionalization of otherwise inert secondary alkyl and benzylic groups by 1,5-hydrogen atom transfer (HAT). Combination of SmI2, a privileged reagent for cascade reactions, and 1,5-HAT can lead to novel complexity-generating radical sequences that unlock access to diverse structures not readily accessible by other means.

Bibliographical metadata

Original languageEnglish
JournalNature Communications
Volume9
Early online date15 Nov 2018
DOIs
Publication statusPublished - 2018

Related information

Researchers

View all