843610-75-3Relevant academic research and scientific papers
Synthesis of the hamigeran skeleton through an electro-oxidative coupling reaction
Sperry, Jeffrey B.,Wright, Dennis L.
, p. 411 - 414 (2007/10/03)
The tricyclic skeleton of the hamigerans has been prepared through an anodic coupling under alcohol-free conditions. The tricyclic core of the hamigerans has been prepared through the use of a two-step electrochemical benzannulation reaction. The annulation proceeds through an initial conjugate addition of a phenethyl cuprate to 3-methylcyclopentenone with in situ silylation of the resulting enolate. Anodic oxidation effectively couples the pendant arene and the silyl enolether to produce a key intermediate for the synthesis of the natural products. Careful optimization revealed that the use of 'alcohol-free' conditions during the electrolysis was critical to obtain high yields of the annulated product. This method allowed the preparation of the tricyclic core of hamigeran A and B in just four steps from commercially available starting materials.
