4b-Aryltetrahydroindeno[1,2-a]indenes by Acid-Catalyzed Transannular Cyclization of Benzannulated Cyclooctene Alcohols
Poonsakdi PloypradithMinistry of Higher Education, Science and Innovation of the Republic of UzbekistanPoramate SongthammawatLaboratory of Medicinal Chemistry, Chulabhorn Research InstituteTanawat PhumjanLaboratory of Medicinal Chemistry, Chulabhorn Research InstituteSomsak RuchirawatCenter of Excellence on Environmental Health and Toxicology, Office of the Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI)
2022en
ABI
Abstract
Abstract By starting from two simple building blocks, benzannulated cyclooctenones were obtained in three steps. Subsequent Grignard/aryl lithium addition to the ketone yielded the corresponding tertiary alcohols that underwent stereoselective acid-catalyzed transannular cyclization to provide a cis-fused 5/5 bicyclic indanylindane framework exclusively. Subsequent stereoselective nucleophilic addition to the indanyl cation by hydride, water, or electron-rich aromatics furnished the 4b-aryltetrahydroindano[1,2-a]indenes in good to excellent yields (up to 92%) in the trans-C9–C9a form in up to a >99:1 diastereomeric ratio.