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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

Author:
Tangdenpaisal, Kassrin, Chuayboonsong, Kanokpish, Ruchirawat, Somsak, Ploypradith, Poonsakdi
Source:
Journal of organic chemistry 2017 v.82 no.5 pp. 2672-2688
ISSN:
1520-6904
Subject:
alcohols, catalysts, chalcones, cycloaddition reactions, diastereoselective synthesis, moieties, olefin, organic chemistry, stereochemistry, stereoselectivity
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.
Agid:
5636163