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Synthesis of the Trans-Syn-Trans Perhydrobenzo[f]chromene Ring System

preprint
submitted on 01.05.2021, 13:10 and posted on 04.05.2021, 12:10 by Amjad Ayad Qatran AlKhdhairawi, Syahrul Imran, Nurhuda Manshoor, Geoffrey A. Cordell, Narendra Babu Shivanagere Nagojappa, Jean-Frédéric Weber

A stereoselective synthesis of the trans-syn-trans perhydrobenzo[f]chromene skeleton is presented. The target compound 3 was achieved in six steps starting from the (S)-(+)-Wieland-Miescher ketone. Key steps include the sp2 alkylation at the a-carbon of an unsaturated ketone, Birch-type reductive alkylation, and an acid-catalyzed cyclization.

History

Email Address of Submitting Author

amjad.khdhairawi@gmail.com

Institution

Taylor's University

Country

Malaysia

ORCID For Submitting Author

0000-0001-7201-2834

Declaration of Conflict of Interest

The authors declare no conflict of interest

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