Alcohols as Efficient Intermolecular Initiators for a Highly Stereoselective Polyene Cyclisation Cascade
Daniya Aynetdinova, Reece Jacques, Kirsten E. Christensen, Timothy J. Donohoe
Abstract
has been shown to trigger a highly stereoselective polyene cyclisation cascade. Three new carbon-carbon bonds are made during the process and complete stereocontrol of up to five new stereogenic centers is observed. The reaction is efficient, has high functional group tolerance and is atom-economic generating water as a stoichiometric by-product. A new polyene substrate-class is employed, and subsequent mechanistic studies indicate a stereoconvergent mechanism. The products of this reaction can be used to synthesize steroid-analogues in a single step.
Topics & Concepts
PolyeneStereoselectivityIntermolecular forceCascadeChemistryOrganic chemistryPolymer chemistryCatalysisMoleculeChromatographySteroid Chemistry and BiochemistryMicrobial Natural Products and BiosynthesisPlant biochemistry and biosynthesis