Journal of the American Chemical Society, Vol.140, No.49, 16909-16913, 2018
Enantioselective Conversion of Oligoprenol Derivatives to Macrocycles in the Germacrene, Cembrene, and 18-Membered Cyclic Sesterterpene Series
A new enantio-and diastereoselective process has been developed for the efficient conversion of farnesol and other oligoprenyl alcohols to chiral 10-, 14-, and 18-membered cyclization products, including germacrenol, (+)-costunolide, 3-beta-elemol, and epi-mukulol. The key cyclization reaction utilizes omega-bromo aldehyde substrates, a chiral ligand, and indium powder as the reagent at -78 degrees C and generates 10-, 14-, and 18 membered cyclic products in 70-74% yield and 94-95% ee.