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

Issued Date

2017-03-03

Resource Type

Article

ISSN

15206904
00223263

DOI

10.1021/acs.joc.6b03086

Other identifier(s)

2-s2.0-85014535472

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.82, No.5 (2017), 2672-2688

Suggested Citation

Kassrin Tangdenpaisal, Kanokpish Chuayboonsong, Somsak Ruchirawat, Poonsakdi Ploypradith 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. Journal of Organic Chemistry. Vol.82, No.5 (2017), 2672-2688. doi:10.1021/acs.joc.6b03086 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/42219

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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

Author(s)

Kassrin Tangdenpaisal
 Kanokpish Chuayboonsong
 Somsak Ruchirawat
 Poonsakdi Ploypradith

Other Contributor(s)

Chulabhorn Research Institute
 Mahidol University
 Chulabhorn Graduate Institute
 Thailand Ministry of Education

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.

Keyword(s)

Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/42219

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Scopus 2016-2017