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 Tangdenpaisal; Kanokpish Chuayboonsong; Somsak Ruchirawat; Poonsakdi Ploypradith

doi:10.1021/acs.joc.6b03086

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

J Org Chem. 2017 Mar 3;82(5):2672-2688. doi: 10.1021/acs.joc.6b03086. Epub 2017 Feb 23.

Authors

Kassrin Tangdenpaisal^{1

2}, Kanokpish Chuayboonsong³, Somsak Ruchirawat^{1

2

3

4}, Poonsakdi Ploypradith^{1

2

3

4}

Affiliations

¹ Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.
² Institute of Molecular Biosciences, Mahidol University , Salaya, Nakhon Pathom, Thailand 73170.
³ Program in Chemical Biology, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210.
⁴ Centre of Excellence on Environmental Health and Toxicology, Commission on Higher Education (CHE), Ministry of Education , Bangkok, Thailand.

PMID: 28186761
DOI: 10.1021/acs.joc.6b03086

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.

Publication types

Research Support, Non-U.S. Gov't