4 years ago

Total Synthesis of Homodimericin A

Total Synthesis of Homodimericin A
Xiaoqiang Lei, Zhen Guo, Yefeng Tang, Juan Feng
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. Taking cues from nature: Homodimericin A, a highly complex fungal metabolite, was synthesized from three readily available building blocks in ten steps (see scheme). The success of the approach hinges on a rationally designed Moore rearrangement to construct the monomeric precursor and a sequence of bioinspired transformations, including homodimerization, Diels–Alder, and carbonyl–ene reactions, to assemble the hexacyclic skeleton.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702893

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