The Total Synthesis of Chondrochloren A

Yannick Linne; Elisa Bonandi; Christopher Tabet; Jan Geldsetzer; Markus Kalesse

doi:10.1002/anie.202016072

The Total Synthesis of Chondrochloren A

Angew Chem Int Ed Engl. 2021 Mar 22;60(13):6938-6942. doi: 10.1002/anie.202016072. Epub 2021 Feb 25.

Authors

Yannick Linne¹, Elisa Bonandi¹, Christopher Tabet¹, Jan Geldsetzer², Markus Kalesse^{1

3

2}

Affiliations

¹ Institute for Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167, Hannover, Germany.
² Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124, Braunschweig, Germany.
³ Centre of Biomolecular Drug Research (BMWZ), Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 38, 30167, Hannover, Germany.

Abstract

The first total synthesis of chondrochloren A is accomplished using a 1,2-metallate rearrangement addition as an alternative for the Nozaki-Hiyama-Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z-enamide is accomplished using a Z-selective cross coupling of the corresponding amide to a Z-vinyl bromide.

Keywords: 1,2-metallate rearrangement; Hoppe anion; chondrochloren; natural product synthesis; polyketides.

Publication types

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