Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A

Po Yuan; Christa K G Gerlinger; Jan Herberger; Tanja Gaich

doi:10.1021/jacs.1c05257

Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A

J Am Chem Soc. 2021 Aug 11;143(31):11934-11938. doi: 10.1021/jacs.1c05257. Epub 2021 Jul 29.

Authors

Po Yuan¹, Christa K G Gerlinger¹, Jan Herberger², Tanja Gaich¹

Affiliations

¹ Institute of Organic Chemistry, University of Konstanz, Universitätsstrasse 10, Konstanz 78464, Germany.
² Institute of Inorganic Chemistry, University of Konstanz, Universitätsstrasse 10, Konstanz 78464, Germany.

PMID: 34324326
DOI: 10.1021/jacs.1c05257

Abstract

The first asymmetric synthesis of pepluanol A (1) is presented. The synthesis route is very concise (10 steps) and features a Curtin-Hammett-driven stereoconvergent intramolecular Diels-Alder reaction. A Nozaki-Hiyama-Kishi reaction comprises the connective step, bringing together the seven-membered enone system bearing the dienophile and the diene in the side chain. Subsequent stereoconvergent IMDA reaction furnishes the carboskeleton of the natural product in only 7 steps. The reactions were carried out on a gram scale up to an advanced intermediate and including the stereoconvergent intramolecular Diels-Alder reaction.

Publication types

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