A new approach towards the synthesis of bielschowskysin: Synthesis and photochemistry of an advanced macrocyclic enedione intermediate

Marko Nesic, Maegen M. Kincanon, David B. Ryffel, David Sarlah

Research output: Contribution to journalArticlepeer-review

Abstract

A novel approach towards bielschowskysin is reported based on an attempted stepwise cyclobutane formation. Synthesis of the key strained framework, containing the tricyclic ring system and all requisite carbons has been developed. While photochemical studies did not result in a late-stage Norrish–Yang cyclization, the observed isomerization could provide important insights into the synthesis of other furanocembranoids.

Original languageEnglish (US)
Article number131318
JournalTetrahedron
Volume76
Issue number51
DOIs
StatePublished - Dec 18 2020

Keywords

  • Bielschowskysin
  • Enedione
  • Furanocembranoids
  • Norrish–Yang
  • Nozaki–Hiyama–Kishi

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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