Total Synthesis of Homodimericin A.
Juan FengXiaoqiang LeiZhen GuoYefeng TangPublished in: Angewandte Chemie (International ed. in English) (2017)
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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