Total Synthesis of Homodimericin A

Angewandte Chemie
Juan FengYefeng Tang

Abstract

We report the concise total synthesis of homodimericin A (1), a recently identified fungal metabolite bearing an unprecedented molecular architecture. The success of the approach hinges on a series of rationally designed and bioinspired transformations, including a Moore rearrangement to assemble the monomeric hydroquinone precursor, homodimerization through double Michael addition to construct the planar A/B/C tricyclic framework, and a tandem Diels-Alder reaction/carbonyl-ene cyclization to forge the congested D/E/F tricyclic cage motif. Unequivocal evidence for the elucidated structure of homodimericin A was also provided by this study.

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Apr 29, 2016·Angewandte Chemie·Chong TianYefeng Tang
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Citations

Nov 24, 2017·Natural Product Reports·Wen-Ju Bai, Xiqing Wang
Dec 16, 2018·Nature Protocols·Yizhou LiuR Thomas Williamson
Jan 21, 2021·Chemical Society Reviews·Jiawei SunWenjun Tang
May 14, 2021·Chemical Communications : Chem Comm·Ryan M BennettDavid C Harrowven
Sep 23, 2021·Accounts of Chemical Research·Ruiyang BaoYefeng Tang

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