A Synthesis of (±)-Aplydactone

Robin Meier, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Aplydactone is an unusual brominated sesquiterpenoid isolated from the sea hare Aplysia dactylomela. Its highly strained skeleton contains two four- and three six-membered rings and features three adjacent quaternary carbon atoms. Although it is most likely of photochemical origin, attempts to generate it from a chamigrane precursor have failed thus far. In this work, we present a total synthesis of aplydactone that relies on two photochemical key steps that are not biomimetic but highly effective in establishing the two cyclobutane rings. Our synthesis also features an unusual Barbier-type cyclization and culminates in new radical conditions to install the sterically hindered secondary bromide of the natural product.

Original languageEnglish (US)
Pages (from-to)11251-11255
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number37
DOIs
StatePublished - 2016

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Cyclobutanes
Cyclization
Biomimetics
Biological Products
Bromides
Carbon
Atoms

Keywords

  • cycloaddition
  • halogenation
  • natural products
  • photochemistry
  • radical reactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

A Synthesis of (±)-Aplydactone. / Meier, Robin; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 55, No. 37, 2016, p. 11251-11255.

Research output: Contribution to journalArticle

Meier, Robin ; Trauner, Dirk. / A Synthesis of (±)-Aplydactone. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 37. pp. 11251-11255.
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