Efficient Synthesis of Polyaromatic Hydrocarbon via a Formal [2+2] Cycloaddition.

Efficient Synthesis of Polyaromatic Hydrocarbon via a Formal [2+2] Cycloaddition. Yakugaku Zasshi. 2016;136(11):1517-1523 Authors: Yamaoka Y Abstract  A potassium base-promoted formal [2+2] cycloaddition of 2-acyl-2'-vinyl-1,1'-biaryls was developed to afford benzo-fused polycyclic cyclobutanols in a highly stereoselective manner. We demonstrated synthesis of substituted polycyclic aromatic hydrocarbons and these heterocyclic derivatives via this cyclization, followed by an acid-promoted rearrangement. Furthermore, asymmetric total synthesis of phenanthroindolizidine alkaloid (-)-tylophorine was achieved using our methodology and late-stage asymmetric hydrogenation of a cyclic imine. PMID: 27803483 [PubMed - in process]
Source: Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan - Category: Drugs & Pharmacology Authors: Tags: Yakugaku Zasshi Source Type: research