Synthesis of (±)-africanol

Abstract

Two diastereomers of africanol, compounds 1a and 1b, were obtained exclusively through a methodology which employed, as the key step, the nBuLi mediated intramolecular cyclization of the vinyl iodide 5. A similar cyclization of 19 provided exclusively the tertiary allylic alcohol 20. Africanol could be prepared, along with its diastereomers 1a and 1b, when ketone 21 was submitted to the cyclization reaction promoted by samarium iodide.

Keywords

• samarium iodide
• cyclization
• africanol
• synthesis