Enantioselective Synthesis of (-)-Halenaquinone

Subir Goswami; Kenichi Harada; Mohamed F El-Mansy; Rajinikanth Lingampally; Rich G Carter

doi:10.1002/anie.201805370

Enantioselective Synthesis of (-)-Halenaquinone

Angew Chem Int Ed Engl. 2018 Jul 16;57(29):9117-9121. doi: 10.1002/anie.201805370. Epub 2018 Jun 19.

Authors

Subir Goswami¹, Kenichi Harada^{1

2}, Mohamed F El-Mansy^{1

3}, Rajinikanth Lingampally¹, Rich G Carter¹

Affiliations

¹ Department of Chemistry, Oregon State University, Corvallis, OR, 97331, USA.
² Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan.
³ Department of Organometallic and Organometalloid Chemistry, National Research Center, Cairo, Egypt.

PMID: 29920904
DOI: 10.1002/anie.201805370

Abstract

The efficient, 12-14 step (LLS) total synthesis of (-)-halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide-catalyzed, Yamada-Otani reaction to establish the C6 all-carbon quaternary stereocenter, (b) multiple, novel palladium-mediated oxidative cyclizations to introduce the furan moiety, and (c) oxidative Bergman cyclization to form the final quinone ring.

Keywords: asymmetric synthesis; organocatalysis; palladium; radical reactions; total synthesis.

Publication types

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