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Updated: Oct 26, 2025
Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A
Po Yuan1, Christa K G Gerlinger1, Jan Herberger2
1Institute of Organic Chemistry, University of Konstanz, Universitätsstrasse 10, Konstanz 78464, Germany.
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.
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