The Total Synthesis of Chalcitrin

Journal of the American Chemical Society
Ming YangScott A Snyder

Abstract

The first total synthesis of the yellow pigment chalcitrin, a structurally distinct pulvinic acid dimer obtained from Chalciporous piperatus, has been achieved in 17 linear steps from commercially available materials. Key elements of the design include the use of a Au(I)-catalyzed Conia ene reaction and an N-heterocyclic carbene-mediated acyloin addition to rapidly fashion its unique polycyclic core, with the two high oxidation state side chains introduced in a single step via a late-stage double Stille coupling. Of note, many alternate designs based on differential final couplings failed, likely because of the hindered nature of the core. In addition, significant challenges in final natural product characterization in terms of matching NMR spectra were experienced; our studies reveal that the originally characterized material was its carboxylate salt form not its free acid.

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Citations

Jul 30, 2021·Journal of the American Chemical Society·Barry M TrostDaniel Zell
Aug 3, 2021·Journal of the American Chemical Society·Pei Qu, Scott A Snyder
Nov 25, 2020·Organic Letters·Nariyoshi Umekubo, Yujiro Hayashi
Dec 29, 2020·Journal of the American Chemical Society·Keitaro MatsuokaShigeki Matsunaga
Feb 11, 2020·Organic Letters·Zhiming YanZhen Yang

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