Proposal: Total Synthesis of Biyouyanagin A

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Presentation transcript:

Proposal: Total Synthesis of Biyouyanagin A Isabelle Bonnaventure, Maude Poirier, Jean-Nicolas Desrosiers, Sébastien Goudreau, Alexandre Côté March 20th, 2007

Retrosynthesis

Hyperolactone C: Chirality Installation

Hyperolactone C: O-H Insertion Entry R Yield (%) 1 Me 86 2 Et 92 3 Bn 91

Hyperolactone C: Carroll Rearrangement

Hyperolactone C: Formation of the Spirolactone Unit

Zingiberene: Chirality Installation

Zingiberene: Cyclization

The [2+2] Approach

When the Steric Hindrance is Increased

Summary