Bioinspired Total Synthesis of Homodimericin A

Angewandte Chemie
Jun HuangZhen Yang

Abstract

Homodimericin A is a remarkable fungal metabolite. This highly oxygenated racemic unsaturated polyketide poses a significant synthetic challenge owing to its sterically demanding central cagelike core containing eight contiguous stereogenic centers (including three quaternary stereocenters) and several carbonyl functionalities. On the basis of its proposed biogenetic synthesis, we designed a total synthesis of homodimericin A that proceeds in seven steps and features a double Michael reaction, an intramolecular Diels-Alder reaction, and an ene reaction.

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Citations

Nov 24, 2017·Natural Product Reports·Wen-Ju Bai, Xiqing Wang
Jan 18, 2019·Chemistry : a European Journal·Teresa E CampanoClaudio Palomo
Dec 16, 2018·Nature Protocols·Yizhou LiuR Thomas Williamson
Apr 30, 2019·Journal of Asian Natural Products Research·Yan-Fei Liu, Shi-Shan Yu
Jan 26, 2021·Chemical Communications : Chem Comm·Gaurav Saini, Manmohan Kapur
Jun 17, 2020·Journal of the American Chemical Society·Zhanchao Meng, Alois Fürstner

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