title: Divergent Strategy for the Diastereoselective Synthesis of the Tricyclic 6,7-Diaryltetrahydro-6H-benzo[c]chromene Core via Pt(IV)-Catalyzed Cycloaddition of o-Quinone Methides and Olefin Ring-Closing Metathesis.
abstract: A divergent strategy for the synthesis of the tricyclic 6,7-diaryltetrahydro-6H-benzo[c]chromene core was successfully developed. The 2,3-trans, 2,4-cis trisubstituted chroman moiety was formed via highly efficient and stereoselective Pt(IV)-catalyzed cycloaddition reactions of the corresponding quinone methides with chalcones. Subsequent steps provided the common diene alcohol, which underwent BF3·Et2O-mediated Et3SiH reduction and olefin ring-closing metathesis (RCM) using Ru(II) catalysts. The sequence of the final two steps provided a handle to diversify the stereochemical outcomes at C6 as well as C10a.
authors.affiliation: Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.|Institute of Molecular Biosciences, Mahidol University , Salaya, Nakhon Pathom, Thailand 73170.
authors.forename: Kassrin
authors.initials: K
authors.lastname: Tangdenpaisal
authors.affiliation: Program in Chemical Biology, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.
authors.forename: Kanokpish
authors.initials: K
authors.lastname: Chuayboonsong
authors.affiliation: Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.|Institute of Molecular Biosciences, Mahidol University , Salaya, Nakhon Pathom, Thailand 73170.|Program in Chemical Biology, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.|Centre of Excellence on Environmental Health and Toxicology, Commission on Higher Education (CHE), Ministry of Education , Bangkok, Thailand.
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat
authors.affiliation: Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.|Institute of Molecular Biosciences, Mahidol University , Salaya, Nakhon Pathom, Thailand 73170.|Program in Chemical Biology, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.|Centre of Excellence on Environmental Health and Toxicology, Commission on Higher Education (CHE), Ministry of Education , Bangkok, Thailand.
authors.forename: Poonsakdi
authors.identifier: 0000-0003-2893-1598
authors.initials: P
authors.lastname: Ploypradith