Asymmetric Total Synthesis of Naphthospironone A

Jia-Xuan Liu; Shi-Peng Zhang; Feng-Sen Sun; Hui Li; Ya-Ling Gong; Shi-Chao Lu; Shu Xu

doi:10.1002/anie.202303229

Asymmetric Total Synthesis of Naphthospironone A

Angew Chem Int Ed Engl. 2023 May 22;62(22):e202303229. doi: 10.1002/anie.202303229. Epub 2023 Apr 19.

Authors

Jia-Xuan Liu¹, Shi-Peng Zhang¹, Feng-Sen Sun¹, Hui Li¹, Ya-Ling Gong¹, Shi-Chao Lu¹, Shu Xu¹

Affiliation

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A Nanwei Road, Xicheng District, Beijing, 100050, China.

PMID: 36952314
DOI: 10.1002/anie.202303229

Abstract

Naphthospironone A, a polyhydroxy cagelike bioactive natural product, was synthesised for the first time in this study. The spiro[bicyclo[3.2.1]octane-pyran] core was constructed by an acid-promoted epoxide-opening lactonisation and a base-induced intramolecular aldol-type cyclisation.

Keywords: Aldol Cyclization; Caged Structure; Naphthoquinone; Natural Products; Total Synthesis.

Abstract

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