Formal Total Synthesis of the Algal Toxin (−)-Polycavernoside A

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Lennart Brewitz; Josep Llaveria; Akira Yada; Alois Fürstner

2013

Scholarcy highlights

  • As a service to our authors and readers, this journal provides supporting information supplied by the authors
  • The chosen route features the arguably most advanced Evans–Tishchenko fragment-coupling process known to date, as well as a striking example of a ring-closing alkyne metathesis reaction in combination with a gold-catalyzed transannular hydroalkoxylation step
  • A concise and largely catalysis-based approach to the potent algal toxin polycavernoside A is described that intercepts a late-stage intermediate of a previous total synthesis; from there on, this challenging target can be reached in a small number of steps
  • The required cyclization precursor 5 was assembled by the arguably most advanced fragment coupling process based on an Evans–Tishchenko redox esterification known to date, which was optimized to the extent that the precious coupling partners could be used in an almost equimolar ratio
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