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

Kassrin TangdenpaisalKanokpish ChuayboonsongSomsak RuchirawatPoonsakdi PloypradithChulabhorn Research InstituteMahidol UniversityChulabhorn Graduate InstituteThailand Ministry of Education2018-12-212019-03-142018-12-212019-03-142017-03-03Journal of Organic Chemistry. Vol.82, No.5 (2017), 2672-268815206904002232632-s2.0-85014535472https://repository.li.mahidol.ac.th/handle/20.500.14594/42219© 2017 American Chemical Society. 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.Mahidol UniversityChemistryDivergent 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 MetathesisArticleSCOPUS10.1021/acs.joc.6b03086