Publication: 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
| dc.contributor.author | Kassrin Tangdenpaisal | en_US |
| dc.contributor.author | Kanokpish Chuayboonsong | en_US |
| dc.contributor.author | Somsak Ruchirawat | en_US |
| dc.contributor.author | Poonsakdi Ploypradith | en_US |
| dc.contributor.other | Chulabhorn Research Institute | en_US |
| dc.contributor.other | Mahidol University | en_US |
| dc.contributor.other | Chulabhorn Graduate Institute | en_US |
| dc.contributor.other | Thailand Ministry of Education | en_US |
| dc.date.accessioned | 2018-12-21T07:12:37Z | |
| dc.date.accessioned | 2019-03-14T08:03:15Z | |
| dc.date.available | 2018-12-21T07:12:37Z | |
| dc.date.available | 2019-03-14T08:03:15Z | |
| dc.date.issued | 2017-03-03 | en_US |
| dc.description.abstract | © 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. | en_US |
| dc.identifier.citation | Journal of Organic Chemistry. Vol.82, No.5 (2017), 2672-2688 | en_US |
| dc.identifier.doi | 10.1021/acs.joc.6b03086 | en_US |
| dc.identifier.issn | 15206904 | en_US |
| dc.identifier.issn | 00223263 | en_US |
| dc.identifier.other | 2-s2.0-85014535472 | en_US |
| dc.identifier.uri | https://repository.li.mahidol.ac.th/handle/20.500.14594/42219 | |
| dc.rights | Mahidol University | en_US |
| dc.rights.holder | SCOPUS | en_US |
| dc.source.uri | https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85014535472&origin=inward | en_US |
| dc.subject | Chemistry | en_US |
| dc.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 | en_US |
| dc.type | Article | en_US |
| dspace.entity.type | Publication | |
| mu.datasource.scopus | https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85014535472&origin=inward | en_US |